Benzoyl-Substituted Serineamides

ABSTRACT

The present invention relates to benzoyl-substituted serineamides of the formula I 
     
       
         
         
             
             
         
       
     
     in which the variables R 1  to R 11  are as defined in the description,
 
and to their agriculturally useful salts,
 
to processes and intermediates for their preparation, and to the use of these compounds or of compositions comprising these compounds for controlling unwanted plants.

The present invention relates to benzoyl-substituted serineamides of theformula I

in which the variables are as defined below:

-   R¹ is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl or    C₁-C₆-haloalkoxy;-   R², R³, R⁴, R⁵ are hydrogen, halogen, cyano, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;-   R⁶, R⁷ are hydrogen, hydroxyl or C₁-C₆-alkoxy;-   R⁸ is C₁-C₆-alkyl, C₁-C₄-cyanoalkyl or C₁-C₆-haloalkyl;-   R⁹ is hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl,    C₃-C₆-alkynyl, C₃-C₆-haloalkenyl, C₃-C₆-haloalkynyl, formyl,    C₁-C₆-alkylcarbonyl, C₃-C₆-cycloalkylcarbonyl,    C₂-C₆-alkenylcarbonyl, C₂-C₆-alkynylcarbonyl, C₁-C₆-alkoxycarbonyl,    C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkynyloxycarbonyl,    C₁-C₆-alkylaminocarbonyl, C₃-C₆-alkenylaminocarbonyl,    C₃-C₆-alkynylaminocarbonyl, C₁-C₆-alkylsulfonylaminocarbonyl,    di-(C₁-C₆-alkyl)aminocarbonyl,    N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl,    N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl,    N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,    N—(C₃-C₆-alkenyl)-N(C₁-C₆-alkoxy)aminocarbonyl,    N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl,    di-(C₁-C₆-alkyl)aminothiocarbonyl, (C₁-C₆-alkyl)cyanoimino,    (amino)cyanoimino, [(C₁-C₆-alkyl)amino]cyanoimino,    [di(C₁-C₆-alkyl)amino]cyanoimino, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl,    C₁-C₆-alkoxyimino-C₁-C₆-alkyl,    N—(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl,    N-(di-C₁-C₆-alkylamino)imino-C₁-C₆-alkyl or tri-C₁-C₄-alkylsilyl,    -   where the alkyl, cycloalkyl and alkoxy radicals mentioned may be        partially or fully halogenated and/or may carry one to three of        the following groups: cyano, hydroxyl, C₃-C₆-cycloalkyl,        C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-alkoxy, C₁-C₄-alkylthio, di-(C₁-C₄-alkyl)amino,        C₁-C₄-alkyl-C₁-C₆-alkoxycarbonylamino, C₁-C₄-alkylcarbonyl,        hydroxycarbonyl, C₁-C₄-alkoxycarbonyl, aminocarbonyl,        C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl or        C₁-C₄-alkylcarbonyloxy;-    phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl,    phenylcarbonyl-C₁-C₆-alkyl, phenoxycarbonyl, phenylaminocarbonyl,    phenylsulfonylaminocarbonyl,    N—(C₁-C₆-alkyl)-N-(phenyl)aminocarbonyl, phenyl-C₁-C₆-alkylcarbonyl,    -   where the phenyl radical may be partially or fully halogenated        and/or may carry one to three of the following groups: nitro,        cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or        C₁-C₄-haloalkoxy; or-    SO₂R¹²;-   R¹⁰ is hydrogen or C₁-C₆-alkyl;-   R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-cyanoalkyl,    C₂-C₆-cyanoalkenyl, C₂-C₆-cyanoalkynyl, C₁-C₆-hydroxyalkyl,    C₂-C₆-hydroxyalkenyl, C₂-C₆-hydroxyalkynyl, C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkenyl, 3- to 6-membered heterocyclyl, 3- to 6-membered    heterocyclyl-C₁-C₄-alkyl,    -   where the cycloalkyl, cycloalkenyl or 3- to 6-membered        heterocyclyl radicals mentioned above may be partially or fully        halogenated and/or may carry one to three radicals from the        group consisting of oxo, cyano, nitro, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, hydroxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        hydroxycarbonyl, C₁-C₆-alkoxycarbonyl,        hydroxycarbonyl-C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkoxy,        amino, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino,        C₁-C₆-alkylsulfonylamino, C₁-C₆-haloalkylsulfonylamino,        aminocarbonylamino, (C₁-C₆-alkylamino)carbonylamino,        di(C₁-C₆-alkyl)aminocarbonylamino, aryl and aryl(C₁-C₆-alkyl);-    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyloxy-C₁-C₄-alkyl,    C₂-C₆-alkynyloxy-C₁-C₄-alkyl, C₁-C₆-haloalkoxy-C₁-C₄-alkyl,    C₂-C₆-haloalkenyloxy-C₁-C₄-alkyl, C₂-C₆-haloalkynyloxy-C₁-C₄-alkyl,    C₁-C₆-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl,    C₂-C₆-alkenylthio-C₁-C₄-alkyl, C₂-C₆-alkynylthio-C₁-C₄-alkyl,    C₁-C₆-haloalkyl-C₁-C₄-thioalkyl, C₂-C₆-haloalkenyl-C₁-C₄-thioalkyl,    C₂-C₈-haloalkynyl-C₁-C₄-thioalkyl, C₁-C₆-alkylsulfinyl-C₁-C₄-alkyl,    C₁-C₆-haloalkylsulfinyl-C₁-C₄-alkyl,    C₁-C₆-alkylsulfonyl-C₁-C₄-alkyl,    C₁-C₆-haloalkylsulfonyl-C₁-C₄-alkyl, amino-C₁-C₄-alkyl,    C₁-C₆-alkylamino-C₁-C₄-alkyl, di(C₁-C₆-alkyl)amino-C₁-C₄-alkyl,    C₁-C₆-alkylsulfonylamino-C₁-C₄-alkyl,    di(C₁-C₆-alkyl)sulfonyl-(C₁-C₆-alkyl)amino-C₁-C₄-alkyl,    C₁-C₆-alkylcarbonyl, hydroxycarbonyl, C₁-C₆-alkoxycarbonyl,    aminocarbonyl, C₁-C₆-alkylaminocarbonyl,    di(C₁-C₆-alkyl)aminocarbonyl, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl,    hydroxycarbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,    C₁-C₆-haloalkoxycarbonyl-C₁-C₄-alkyl,    C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl, aminocarbonyl-C₁-C₄-alkyl,    C₁-C₆-alkylaminocarbonyl-C₁-C₄-alkyl,    di(C₁-C₆-alkyl)aminocarbonyl-C₁-C₄-alkyl, formylamino-C₁-C₄-alkyl,-    C₁-C₆-alkoxycarbonylamino-C₁-C₄-alkyl,    C₁-C₆-alkylcarbonylamino-C₁-C₄-alkyl,    C₁-C₆-alkylcarbonyl-(C₁-C₆-alkylamino)-C₁-C₄-alkyl,    [(C₁-C₆-alkyl)aminocarbonyloxy]C₁-C₄-alkyl,    [di(C₁-C₆-alkyl)aminocarbonyloxy]C₁-C₄-alkyl,    {di[di(C₁-C₆-alkyl)amino]carbonyloxy}C₁-C₄-alkyl,    [(C₁-C₆-alkyl)aminocarbonylamino]-C₁-C₄-alkyl,    [di(C₁-C₆-alkyl)aminocarbonylamino]-C₁-C₄-alkyl;-    phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl, phenyl-C₂-C₄-alkynyl,    phenyl-C₁-C₄-haloalkyl, phenyl-C₂-C₄-haloalkenyl,    phenyl-C₂-C₄-haloalkynyl, phenyl-C₁-C₄-hydroxyalkyl,    phenyl-C₂-C₄-hydroxyalkenyl, phenyl-C₂-C₄-hydroxyalkynyl,    phenylcarbonyl-C₁-C₄-alkyl, phenylcarbonyloxy-C₁-C₄-alkyl,    phenylcarbonylamino-C₁-C₄-alkyl, phenyloxycarbonyl-C₁-C₄-alkyl,    phenyloxy-C₁-C₄-alkyl, phenylthio-C₁-C₄-alkyl,    phenylsulfinyl-C₁-C₄-alkyl, phenylsulfonyl-C₁-C₄-alkyl,-    heteroaryl-C₁-C₄-alkyl, heteroaryl-C₂-C₄-alkenyl,    heteroaryl-C₂-C₄-alkynyl, heteroaryl-C₁-C₄-haloalkyl,    heteroaryl-C₂-C₄-haloalkenyl, heteroaryl-C₂-C₄-haloalkynyl,    heteroaryl-C₁-C₄-hydroxyalkyl, heteroaryl-C₂-C₄-hydroxyalkenyl,    heteroaryl-C₂-C₄-hydroxyalkynyl, heteroarylcarbonyl-C₁-C₄-alkyl,    heteroarylcarbonyloxy-C₁-C₄-alkyl,    heteroaryloxycarbonyl-C₁-C₄-alkyl, heteroaryloxy-C₁-C₄-alkyl,    heteroarylthio-C₁-C₄-alkyl, heteroarylsulfinyl-C₁-C₄-alkyl,    heteroarylsulfonyl-C₁-C₄-alkyl,    -   where the phenyl and heteroaryl radicals mentioned above may be        partially or fully halogenated and/or may carry one to three        radicals from the group consisting of cyano, nitro, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, hydroxy, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        hydroxycarbonyl, C₁-C₆-alkoxycarbonyl,        hydroxycarbonyl-C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkoxy,        amino, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino,        C₁-C₆-alkylsulfonylamino, C₁-C₆-haloalkylsulfonylamino,        (C₁-C₆-alkylamino)carbonylamino,        di(C₁-C₆-alkyl)aminocarbonylamino, aryl and aryl(C₁-C₆-alkyl);-   R¹² is C₁-C₆-alkyl, C₁-C₆-haloalkyl or phenyl,    -   where the phenyl radical may be partially or fully halogenated        and/or may carry one to three of the following groups:        C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₁-C₆-alkoxy;        and their agriculturally useful salts.

Moreover, the invention relates to processes and intermediates forpreparing compounds of the formula I, to compositions comprising themand to the use of these derivatives or of the compositions comprisingthem for controlling harmful plants.

Fungicidally effective thienyl-substituted amino acid derivatives whichcarry an optionally hydroxyl- or alkoxy-substituted alkyl radical in theα-position are described inter alia in EP 450 355.

Also known from the literature, for example from U.S. Pat. No.5,346,907, WO 96/012499 and WO 02/069905, are serine derivatives havingpharmaceutical activity which may carry in the α-position an optionallyhydroxyl- or alkoxy-substituted alkyl radical, inter alia.

However, the herbicidal properties of the prior-art compounds and/ortheir compatibility with crop plants are not entirely satisfactory.

Accordingly, it is an object of the present invention to provide novel,in particular herbicidally active, compounds having improved properties.

We have found that this object is achieved by the benzoyl-substitutedserineamides of the formula I and their herbicidal action.

Furthermore, we have found herbicidal compositions which comprise thecompounds I and have very good herbicidal action. Moreover, we havefound processes for preparing these compositions and methods forcontrolling unwanted vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula Icomprise two or more centers of chirality, in which case they arepresent as enantiomers or diastereomer mixtures. The invention providesboth the pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I may also be present in the form of theiragriculturally useful salts, the nature of the salt generally beingimmaterial. Suitable salts are, in general, the cations or the acidaddition salts of those acids whose cations and anions, respectively,have no adverse effect on the herbicidal action of the compounds I.

Suitable cations are in particular ions of the alkali metals, preferablylithium, sodium and potassium, of the alkaline earth metals, preferablycalcium and magnesium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium, where, if desired,one to four hydrogen atoms may be replaced by C₁-C₄-alkyl,hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropylammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,di-(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate, and the anions of C₁-C₄-alkanoic acids,preferably formate, acetate, propionate and butyrate.

The organic moieties mentioned for the substituents R¹-R¹² or asradicals on phenyl, aryl, heteroaryl or heterocyclyl rings arecollective terms for individual enumerations of the specific groupmembers. All hydrocarbon chains, i.e. all alkyl, alkylsilyl, alkenyl,alkynyl, cyanoalkyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy,haloalkoxy, alkoxyalkyl, alkoxyalkoxyalkyl, alkylcarbonyl,alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl,alkynyloxycarbonyl, alkylamino, alkylsulfonylamino,haloalkylsulfonylamino, alkylalkoxycarbonylamino, alkylaminocarbonyl,alkenylaminocarbonyl, alkynylaminocarbonyl, alkylsulfonylaminocarbonyl,dialkylaminocarbonyl, N-alkenyl-N-alkylaminocarbonyl,N-alkynyl-N-alkylamino-carbonyl, N-alkoxy-N-alkylaminocarbonyl,N-alkenyl-N-alkoxyaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl,dialkylaminothiocarbonyl, alkylcarbonylalkyl, alkoximinoalkyl,N-(alkylamino)iminoalkyl, N-(dialkylamino)iminoalkyl, alkylcyanoimino,alkylaminocyanoimino, dialkylaminocyanoimino, formylaminoalkyl,alkoxycarbonylaminoalkyl, (alkylamino)carbonyloxyalkyl,(alkylamino)carbonylaminoalkyl, (dialkylamino)carbonylaminoalkyl,phenylcarbonylaminoalkyl, phenylalkyl, phenylcarbonylalkyl,N-alkyl-N-phenylaminocarbonyl, phenylalkylcarbonyl, arylalkyl,heterocyclylalkyl, heterocyclylcarbonylalkyl,N-alkyl-N-heterocyclylaminocarbonyl, heterocyclylalkylcarbonyl,alkylthio and alkylcarbonyloxy moieties, may be straight-chain orbranched.

Unless indicated otherwise, halogenated substituents preferably carryone to five identical or different halogen atoms. The term halogendenotes in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

-   -   C₁-C₄-alkyl and also the alkyl moieties of tri-C₁-C₄-alkylsilyl,        C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl-C₁-C₄-alkoxycarbonylamino,        C₁-C₄-alkyliminooxy-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,        C₂-C₆-alkenyloxy-C₁-C₄-alkyl, C₂-C₆-alkynyloxy-C₁-C₄-alkyl,        C₁-C₆-haloalkoxy-C₁-C₄-alkyl, C₂-C₆-haloalkenyloxy-C₁-C₄-alkyl,        C₂-C₆-haloalkynyloxy-C₁-C₄-alkyl,        C₁-C₆-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₆-alkylthio-C₁-C₄-alkyl, C₂-C₆-alkenylthio-C₁-C₄-alkyl,        C₂-C₆-alkynylthio-C₁-C₄-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₄-alkyl,        C₁-C₆-haloalkylsulfinyl-C₁-C₄-alkyl,        C₁-C₆-alkylsulfonyl-C₁-C₄-alkyl,        C₁-C₆-haloalkylsulfonyl-C₁-C₄-alkyl, amino-C₁-C₄-alkyl,        C₁-C₆-alkylamino-C₁-C₄-alkyl, di(C₁-C₆-alkyl)amino-C₁-C₄-alkyl,        formylamino-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonylamino-C₁-C₄-alkyl,        C₁-C₆-alkylsulfonylamino-C₁-C₄-alkyl,        C₁-C₆-alkylsulfonyl-(C₁-C₆-alkylamino)-C₁-C₄-alkyl,        hydroxycarbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,        C₁-C₆-haloalkoxycarbonyl-C₁-C₄-alkyl,        C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl, aminocarbonyl-C₁-C₄-alkyl,        C₁-C₆-alkylaminocarbonyl-C₁-C₄-alkyl,        di(C₁-C₆-alkyl)aminocarbonyl-C₁-C₄-alkyl,        [(C₁-C₆-alkyl)aminocarbonylamino]-C₁-C₄-alkyl,        [di(C₁-C₆-alkyl)aminocarbonylamino]-C₁-C₄-alkyl,        C₁-C₆-alkylcarbonylamino-C₁-C₄-alkyl,        C₁-C₆-alkylcarbonyl-(C₁-C₆-alkylamino)-C₁-C₄-alkyl,        [(C₁-C₆-alkyl)aminocarbonyloxy]-C₁-C₄-alkyl,        [di(C₁-C₆-alkyl)aminocarbonyloxy]C₁-C₄-alkyl,        {di[di(C₁-C₆-alkyl)amino]carbonyloxy}C₁-C₄-alkyl,        heterocyclyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkyl,        phenylcarbonylamino-C₁-C₄-alkyl, phenyl-C₁-C₄-alkyl,        phenylcarbonyl-C₁-C₄-alkyl, heteroarylcarbonyl-C₁-C₄-alkyl,        heteroarylcarbonyloxy-C₁-C₄-alkyl,        heteroaryloxycarbonyl-C₁-C₄-alkyl, heteroaryloxy-C₁-C₄-alkyl,        heteroarylthio-C₁-C₄-alkyl, heteroarylsulfinyl-C₁-C₄-alkyl,        heteroarylsulfonyl-C₁-C₄-alkyl, and aryl-(C₁-C₄-alkyl): for        example methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,        1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;    -   C₁-C₆-alkyl and also the alkyl moieties of C₁-C₆-cyanoalkyl,        C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonylamino,        C₁-C₆-alkylsulfonylaminocarbonyl,        N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl,        (C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl,        N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,        C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl,        N—(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl,        N-(di-C₁-C₆-alkylamino)imino-C₁-C₆-alkyl,        (C₁-C₆-alkyl)cyanoimino, phenyl-C₁-C₆-alkyl,        phenylcarbonyl-C₁-C₆-alkyl,        N—(C₁-C₆-alkyl)-N-phenylaminocarbonyl, heterocyclyl-C₁-C₆-alkyl,        heterocyclylcarbonyl-C₁-C₆-alkyl and        N—(C₁-C₆-alkyl)-N-heterocyclylaminocarbonyl:        -   C₁-C₄-alkyl as mentioned above, and also, for example,            n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,            2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl,            1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,            2-methylpentyl, 3-methylpentyl, 4-methylpentyl,            1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-di-methylbutyl,            2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,            1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,            1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;    -   C₁-C₄-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl,        propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl,        1-methylpropylcarbonyl, 2-methylpropylcarbonyl or        1,1-dimethylethylcarbonyl;    -   C₁-C₆-alkylcarbonyl and also the alkylcarbonyl radicals of        C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl,        C₁-C₆-alkylcarbonyloxy-C₁-C₆-alkyl,        C₁-C₆-alkylcarbonylamino-C₁-C₄-alkyl, phenyl-C₁-C₆-alkylcarbonyl        and heterocyclyl-C₁-C₆-alkylcarbonyl,        C₁-C₆-alkylcarbonyl-(C₁-C₆-alkylamino)-C₁-C₄-alkyl:        -   C₁-C₄-alkylcarbonyl as mentioned above, and also, for            example, pentylcarbonyl, 1-methylbutylcarbonyl,            2-methylbutylcarbonyl, 3-methylbutylcarbonyl,            2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl,            hexylcarbonyl, 1,1-dimethylpropylcarbonyl,            1,2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl,            2-methylpentylcarbonyl, 3-methylpentylcarbonyl,            4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl,            1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl,            2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl,            3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl,            2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl,            1,2,2-trimethylpropylcarbonyl,            1-ethyl-1-methylpropylcarbonyl or            1-ethyl-2-methylpropylcarbonyl;    -   C₃-C₆-cycloalkyl and also the cycloalkyl moieties of        C₃-C₆-cycloalkylcarbonyl: monocyclic saturated hydrocarbons        having 3 to 6 ring members, such as cyclopropyl, cyclobutyl,        cyclopentyl and cyclohexyl;    -   C₃-C₆-cycloalkenyl: for example 1-cyclopropenyl,        2-cyclopropenyl, 1-cyclobutenyl, 2-cyclobutenyl,        1-cyclopentenyl, 2-cyclopentenyl, 1,3-cyclopentadienyl,        1,4-cyclopentadienyl, 2,4-cyclopentadienyl, 1-cyclohexenyl,        2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl,        1,4-cyclohexadienyl, 2,5-cyclohexadienyl;    -   C₃-C₆-alkenyl and also the alkenyl moieties of        C₃-C₆-alkenyloxycarbonyl, C₃-C₆-alkenylaminocarbonyl,        N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl and        N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl: for example        1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,        3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,        1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl,        2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl,        2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl,        2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,        2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,        1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl,        1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,        3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,        2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl,        1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl,        4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,        3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,        2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,        1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,        1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,        1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,        1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,        2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,        2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,        3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,        1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,        2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,        1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,        1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;    -   C₂-C₆-alkenyl and also the alkenyl moieties of        C₂-C₆-alkenylcarbonyl, C₂-C₆-alkenyloxy-C₁-C₄-alkyl,        C₂-C₆-alkenylthio-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl,        heteroary-C₂-C₄-alkenyl: C₃-C₆-alkenyl as mentioned above, and        also ethenyl;    -   C₃-C₆-alkynyl and also the alkynyl moieties of        C₃-C₆-alkynyloxycarbonyl, C₃-C₆-alkynylaminocarbonyl,        N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl,        N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl: for example        1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,        1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl,        4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,        2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,        1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,        5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,        1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,        3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,        4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl,        1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,        2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,        1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and        1-ethyl-1-methyl-2-propynyl;    -   C₂-C₆-alkynyl and also the alkynyl moieties of        C₂-C₆-alkynylcarbonyl, C₂-C₂-alkynyloxy-C₁-C₄-alkyl,        C₂-C₆-alkynylthio-C₁-C₄-alkyl, phenyl-C₂-C₄-alkynyl,        heteroaryl-C₂-C₄-alkynyl: C₃-C₆-alkynyl as mentioned above, and        also ethynyl;    -   C₁-C₄-cyanoalkyl: for example cyanomethyl, 1-cyanoeth-1-yl,        2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl,        3-cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl,        1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl,        4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl,        1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methylprop-3-yl,        2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl and        2-cyanomethylprop-2-yl;    -   C₁-C₄-hydroxyalkyl and also the C₁-C₄-hydroxyalkyl moieties of        phenyl-C₁-C₄-hydroxyalkyl, heteroaryl-C₁-C₄-hydroxyalkyl: for        example hydroxymethyl, 1-hydroxyeth-1-yl, 2-hydroxyeth-1-yl,        1-hydroxyprop-1-yl, 2-hydroxyprop-1-yl, 3-hydroxyprop-1-yl,        1-hydroxyprop-2-yl, 2-hydroxyprop-2-yl, 1-hydroxybut-1-yl,        2-hydroxybut-1-yl, 3-hydroxybut-1-yl, 4-hydroxybut-1-yl,        1-hydroxybut-2-yl, 2-hydroxybut-2-yl, 1-hydroxybut-3-yl,        2-hydroxybut-3-yl, 1-hydroxy-2-methylprop-3-yl,        2-hydroxy-2-methylprop-3-yl, 3-hydroxy-2-methylprop-3-yl and        2-hydroxymethylprop-2-yl, 1,2-dihydroxyethyl,        1,2-dihydroxyprop-3-yl, 2,3-dihydroxyprop-3-yl,        1,2-dihydroxyprop-2-yl, 1,2-dihydroxybut-4-yl,        2,3-dihydroxybut-4-yl, 3,4-dihydroxybut-4-yl,        1,2-dihydroxybut-2-yl, 1,2-dihydroxybut-3-yl,        2,3-dihydroxybut-3-yl, 1,2-dihydroxy-2-methylprop-3-yl,        2,3-dihydroxy-2-methylprop-3-yl;    -   C₁-C₆-hydroxyalkyl: C₁-C₄-hydroxyalkyl as mentioned above, and        also for example 1-hydroxypent-5-yl, 2-hydroxypent-5-yl,        3-hydroxypent-5-yl, 4-hydroxypent-5-yl, 5-hydroxypent-5-yl,        1-hydroxypent-4-yl, 2-hydroxypent-4-yl, 3-hydroxypent-4-yl,        4-hydroxypent-4-yl, 1-hydroxypent-3-yl, 2-hydroxypent-3-yl,        3-hydroxypent-3-yl, 1-hydroxy-2-methylbut-3-yl,        2-hydroxy-2-methylbut-3-yl, 3-hydroxy-2-methylbut-3-yl,        1-hydroxy-2-methylbut-4-yl, 2-hydroxy-2-methylbut-4-yl,        3-hydroxy-2-methylbut-4-yl, 4-hydroxy-2-methylbut-4-yl,        1-hydroxy-3-methylbut-4-yl, 2-hydroxy-3-methylbut-4-yl,        3-hydroxy-3-methylbut-4-yl, 4-hydroxy-3-methylbut-4-yl,        1-hydroxyhex-6-yl, 2-hydroxyhex-6-yl, 3-hydroxy-hex-6-yl,        4-hydroxy-hex-6-yl, 5-hydroxyhex-6-yl, 6-hydroxyhex-6-yl,        1-hydroxy-2-methylpent-5-yl, 2-hydroxy-2-methylpent-5-yl,        3-hydroxy-2-methylpent-5-yl, 4-hydroxy-2-methylpent-5-yl,        5-hydroxy-2-methylpent-5-yl, 1-hydroxy-3-methylpent-5-yl,        2-hydroxy-3-methylpent-5-yl, 3-hydroxy-3-methylpent-5-yl,        4-hydroxy-3-methylpent-5-yl, 5-hydroxy-3-methylpent-5-yl,        1-hydroxy-4-methylpent-5-yl, 2-hydroxy-4-methylpent-5-yl,        3-hydroxy-4-methylpent-5-yl, 4-hydroxy-4-methylpent-5-yl,        5-hydroxy-4-methylpent-5-yl, 1-hydroxy-5-methylpent-5-yl,        2-hydroxy-5-methylpent-5-yl, 3-hydroxy-5-methylpent-5-yl,        4-hydroxy-5-methylpent-5-yl, 5-hydroxy-5-methylpent-5-yl,        1-hydroxy-2,3-dimethylbut-4-yl, 2-hydroxy-2,3-dimethylbut-4-yl,        3-hydroxy-2,3-dimethylbut-4-yl, 4-hydroxy-2,3-dimethylbut-4-yl,        1,2-dihydroxypent-5-yl, 2,3-dihydroxypent-5-yl,        3,4-dihydroxypent-5-yl, 4,5-dihydroxypent-5-yl,        1,2-dihydroxypent-4-yl, 2,3-dihydroxypent-4-yl,        3,4-dihydroxypent-4-yl, 4,5-dihydroxypent-4-yl,        1,2-dihydroxypent-3-yl, 2,3-dihydroxypent-3-yl,        1,2-dihydroxy-2-methylbut-3-yl, 2,3-dihydroxy-2-methylbut-3-yl,        3,4-dihydroxy-2-methylbut-3-yl,        2-hydroxy-2-hdroxymethylbut-3-yl,        1,2-dihydroxy-2-methylbut-4-yl, 2,3-dihydroxy-2-methylbut-4-yl,        3,4-dihydroxy-2-methylbut-4-yl, 1,2-dihydroxy-3-methylbut-4-yl,        2,3-dihydroxy-3-methylbut-4-yl, 3,4-dihydroxy-3-methylbut-4-yl,        3-hydroxy-3-hydroxymethylbut-4-yl, 1,2-dihydroxyhex-6-yl,        2,3-dihydroxyhex-6-yl, 3,4-dihydroxyhex-6-yl,        4,5-dihydroxyhex-6-yl, 5,6-dihydroxyhex-6-yl,        1,2-dihydroxy-2-methylpent-5-yl,        2,3-dihydroxy-2-methylpent-5-yl,        3,4-dihydroxy-2-methylpent-5-yl,        4,5-dihydroxy-2-methylpent-5-yl,        2-hydroxy-2-hdroxymethylpent-5-yl,        1,2-dihydroxy-3-methylpent-5-yl,        2,3-dihydroxy-3-methylpent-5-yl,        3,4-dihydroxy-3-methylpent-5-yl,        4,5-dihydroxy-3-methylpent-5-yl,        3-hydroxy-3-hydroxymethylpent-5-yl,        1,2-dihydroxy-4-methylpent-5-yl,        2,3-dihydroxy-4-methylpent-5-yl,        3,4-dihydroxy-4-methylpent-5-yl,        4,5-dihydroxy-4-methylpent-5-yl,        4-hydroxy-4-hydroxymethylpent-5-yl,        1,2-dihydroxy-5-methylpent-5-yl,        2,3-dihydroxy-5-methylpent-5-yl,        3,4-dihydroxy-5-methylpent-5-yl,        4,5-dihydroxy-5-methylpent-5-yl,        5-hydroxy-5-hydroxymethylpent-5-yl,        1,2-dihydroxy-2,3-dimethylbut-4-yl,        2,3-dihydroxy-2,3-dimethylbut-4-yl,        3,4-dihydroxy-2,3-dimethylbut-4-yl,        2-hydroxy-2-hydroxymethyl-3-methylbut-4-yl,        3-hydroxy-3-hydroxymethyl-2-methylbut-4-yl;    -   C₁-C₄-haloalkyl and also the haloalkyl moieties of        phenyl-C₁-C₄-haloalkyl, heteroaryl-C₁-C₄-haloalkyl: a        C₁-C₄-alkyl radical as mentioned above which is partially or        fully substituted by fluorine, chlorine, bromine and/or iodine,        i.e., for example, chloromethyl, dichloromethyl,        trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,        chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,        bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl,        2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,        2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,        2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,        2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,        3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,        2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,        2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,        3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,        heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,        1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,        4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl,        1,1,2,2-tetrafluoroethyl and        1-trifluoromethyl-1,1,2,2-tetrafluoroethyl;    -   C₁-C₆-haloalkyl and also the haloalkyl moieties of        C₁-C₆-haloalkylsulfonylamino, C₁-C₆-haloalkyl-C₁-C₄-thioalkyl:        C₁-C₄-haloalkyl as mentioned above, and also, for example,        5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,        undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,        6-iodohexyl and dodecafluorohexyl;    -   C₃-C₆-haloalkenyl: a C₃-C₆-alkenyl radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, for example 2-chloroprop-2-en-1-yl,        3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl,        3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2-en-1-yl,        2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl,        3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1-yl,        3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1-yl or        2,3-dibromobut-2-en-1-yl;    -   C₂-C₆-haloalkenyl and also the C₂-C₆-haloalkenyl moieties of        C₂-C₆-haloalkenyloxy-C₁-C₄-alkyl,        C₂-C₆-haloalkenyl-C₁-C₄-thioalkyl, phenyl-C₂-C₄-haloalkenyl,        heteroaryl-C₂-C₄-haloalkenyl: a C₂-C₆-alkenyl radical as        mentioned above which is partially or fully substituted by        fluorine, chlorine, bromine and/or iodine: for example        2-chlorovinyl, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl,        3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl,        2-bromovinyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl,        3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;    -   C₂-C₆-cyanoalkenyl: for example 2-cyanovinyl, 2-cyanoallyl,        3-cyanoallyl, 2,3-dicyanoallyl, 3,3-dicyanoallyl,        2,3,3-tricyanoallyl, 2,3-dicyanobut-2-enyl;    -   C₂-C₆-hydroxyalkenyl and also the hydroxy moieties of        phenyl-C₁-C₄-hydroxyalkenyl, heteroaryl-C₁-C₄-hydroxyalkenyl:        for example 2-hydroxyvinyl, 2-hydroxyallyl, 3-hydroxyallyl,        2,3-dihydroxyallyl, 3,3-dihydroxyallyl, 2,3,3-trihydroxyallyl,        2,3-dihydroxybut-2-enyl;    -   C₃-C₆-haloalkynyl: a C₃-C₆-alkynyl radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, for example 1,1-difluoroprop-2-yn-1-yl,        3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl,        4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl,        4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl,        5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or        6-iodohex-5-yn-1-yl;    -   C₂-C₆-haloalkynyl and also the C₂-C₆-haloalkynyl moieties of        C₂-C₆-haloalkynyloxy-C₁-C₄-alkyl,        C₂-C₆-haloalkynyl-C₁-C₄-thioalkyl, phenyl-C₂-C₄-haloalkynyl,        heteroaryl-C₂-C₄-haloalkynyl: a C₂-C₆-alkynyl radical as        mentioned above which is partially or fully substituted by        fluorine, chlorine, bromine and/or iodine, for example        1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl,        4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl,        1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl,        5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl,        6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;    -   C₂-C₆-cyanoalkynyl: for example 1,1-dicyanoprop-2-yn-1-yl,        3-cyanoprop-2-yn-1-yl, 4-cyano-but-2-yn-1-yl,        1,1-dicyanobut-2-yn-1-yl, 4-cyanobut-3-yn-1-yl,        5-cyanopent-3-yn-1-yl, 5-cyanopent-4-yn-1-yl,        6-cyanohex-4-yn-1-yl or 6-cyanohex-5-yn-1-yl;    -   C₂-C₆-hydroxyalkynyl and also the hydroxy moieties of        phenyl-C₂-C₄-hydroxyalkynyl: for example        1,1-dihydroxyprop-2-yn-1-yl, 3-hydroxyprop-2-yn-1-yl,        4-hydroxybut-2-yn-1-yl, 1,1-dihydroxybut-2-yn-1-yl,        4-hydroxybut-3-yn-1-yl, 5-hydroxypent-3-yn-1-yl,        5-hydroxypent-4-yn-1-yl, 6-hydroxyhex-4-yn-1-yl or        6-hydroxyhex-5-yn-1-yl;    -   C₁-C₆-alkylsulfinyl (C₁-C₆-alkyl-S(═O)—) and also the        C₁-C₆-alkylsulfinyl moieties of C₁-C₆-alkylsulfinyl-C₁-C₄-alkyl:        for example methylsulfinyl, ethylsulfinyl, propylsulfinyl,        1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl,        2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl,        pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl,        3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl,        1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl,        1,2-dimethylpropylsulfinyl, hexylsulfinyl,        1-methylpentylsulfinyl, 2-methylpentylsulfinyl,        3-methylpentylsulfinyl, 4-methylpentylsulfinyl,        1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,        1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,        2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,        1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,        1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,        1-ethyl-1-methylpropylsulfinyl and        1-ethyl-2-methylpropylsulfinyl;    -   C₁-C₆-haloalkylsulfinyl and also the C₁-C₆-haloalkylsulfinyl        moieties of C₁-C₆-haloalkylsulfinyl-C₁-C₄-alkyl:        C₁-C₆-alkylsulfinyl radical as mentioned above which is        partially or fully substituted by fluorine, chlorine, bromine        and/or iodine, i.e. for example fluoromethylsulfinyl,        difluoromethylsulfinyl, trifluoromethylsulfinyl,        chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl,        2-fluoroethylsulfinyl, 2-chloroethylsulfinyl,        2-bromoethylsulfinyl, 2-iodoethylsulfinyl,        2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl,        2,2,2-trichloroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl,        2-chloro-2,2-difluoroethylsulfinyl,        2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,        2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl,        2-chloropropylsulfinyl, 3-chloropropylsulfinyl,        2-bromopropylsulfinyl, 3-bromopropylsulfinyl,        2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,        2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,        3,3,3-trichloropropylsulfinyl,        2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl,        1-(fluoromethyl)-2-fluoroethylsulfinyl,        1-(chloromethyl)-2-chloroethylsulfinyl,        1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,        4-chlorobutylsulfinyl, 4-bromobutylsulfinyl,        nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl,        5-chloropentylsulfinyl, 5-bromopentylsulfinyl,        5-iodopentylsulfinyl, undecafluoropentylsulfinyl,        6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl,        6-bromohexylsulfinyl, 6-iodohexylsulfinyl and        dodecafluorohexylsulfinyl;    -   C₁-C₆-alkylsulfonyl (C₁-C₆-alkyl-S(O)₂—) and also the        C₁-C₆-alkylsulfonyl moieties of C₁-C₆-alkylsulfonyl-C₁-C₄-alkyl,        C₁-C₆-alkylsulfonylamino, C₁-C₆-alkylsulfonylamino-C₁-C₄-alkyl,        C₁-C₆-alkylsulfonyl-(C₁-C₆-alkylamino)-C₁-C₄-alkyl: for example        methylsulfonyl, ethylsulfonyl, propylsulfonyl,        1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl,        2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl,        pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl,        3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl,        1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl,        1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl,        2-methylpentylsulfonyl, 3-methylpentylsulfonyl,        4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,        1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,        2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,        3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl,        2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl,        1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl        and 1-ethyl-2-methylpropylsulfonyl;    -   C₁-C₆-haloalkylsulfonyl and also the C₁-C₆-haloalkylsulfonyl        moieties of C₁-C₆-haloalkylsulfonyl-C₁-C₄-alkyl,        C₁-C₆-haloalkylsulfonylamino: a C₁-C₆-alkylsulfonyl radical as        mentioned above which is partially or fully substituted by        fluorine, chlorine, bromine and/or iodine, i.e. for example        fluoromethylsulfonyl, difluoromethylsulfonyl,        trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl,        bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl,        2-chloroethylsulfonyl, 2-bromoethylsulfonyl,        2-iodoethylsulfonyl, 2,2-difluoroethyl-sulfonyl,        2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,        2-chloro-2,2-difluoroethylsulfonyl,        2,2-dichloro-2-fluoroethylsulfonyl,        2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,        2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,        2-chloropropylsulfonyl, 3-chloropropylsulfonyl,        2-bromopropylsulfonyl, 3-bromopropylsulfonyl,        2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,        2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,        3,3,3-trichloropropylsulfonyl,        2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl,        1-(fluoromethyl)-2-fluoroethylsulfonyl,        1-(chloromethyl)-2-chloroethylsulfonyl,        1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,        4-chlorobutylsulfonyl, 4-bromobutylsulfonyl,        nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl,        5-chloropentylsulfonyl, 5-bromopentylsulfonyl,        5-iodopentylsulfonyl, 6-fluorohexylsulfonyl,        6-bromohexylsulfonyl, 6-iodohexylsulfonyl and        dodecafluorohexylsulfonyl;    -   C₁-C₄-alkoxy and also the alkoxy moieties of        hydroxycarbonyl-C₁-C₄-alkoxy, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl and        C₁-C₄-alkyl-C₁-C₄-alkoxycarbonylamino: for example methoxy,        ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy,        2-methylpropoxy and 1,1-dimethylethoxy;    -   C₁-C₆-alkoxy and also the alkoxy moieties of        hydroxycarbonyl-C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkoxy,        N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,        N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl,        N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl and        C₁-C₆-alkoxyimino-C₁-C₆-alkyl: C₁-C₄-alkoxy as mentioned above,        and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy,        3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy,        2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy,        2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,        1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,        2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,        1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,        1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and        1-ethyl-2-methylpropoxy;    -   C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, i.e., for example, fluoromethoxy,        difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,        bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,        2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,        2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,        2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,        2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,        3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,        2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy,        2,3-difluoropropoxy, 2,3-dichloropropoxy,        3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,        2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,        1-(fluoromethyl)-2-fluoroethoxy,        1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy,        4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and        nonafluorobutoxy;    -   C₁-C₆-haloalkoxy and also the C₁-C₆-haloalkoxy moieties of        C₁-C₆-haloalkoxy-C₁-C₄-alkyl,        C₁-C₆-haloalkoxycarbonyl-C₁-C₄-alkyl: C₁-C₄-haloalkoxy as        mentioned above, and also, for example, 5-fluoropentoxy,        5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy,        undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy,        6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;    -   C₁-C₆-alkoxy-C₁-C₄-alkyl and also the C₁-C₆-alkoxy-C₁-C₄-alkyl        moieties of C₁-C₆-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl: C₁-C₄-alkyl        which is substituted by C₁-C₆-alkoxy as mentioned above, i.e.,        for example, methoxymethyl, ethoxymethyl, propoxymethyl,        (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl,        (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl,        2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl,        2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl,        2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,        2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl,        2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl,        2-(butoxy)propyl, 2-(1-methylpropoxy)propyl,        2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl,        3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl,        3-(1-methylethoxy)propyl, 3-(butoxy)propyl,        3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,        3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,        2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl,        2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,        2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,        3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,        3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,        3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,        4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,        4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl and        4-(1,1-dimethylethoxy)butyl;    -   C₁-C₄-alkoxycarbonyl and also the alkoxycarbonyl moieties of        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₄-alkoxycarbonyl and        di-(C₁-C₄-alkyl)amino-C₁-C₄-alkoxycarbonyl: for example        methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl,        1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl,        2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;    -   C₁-C₆-alkoxycarbonyl and also the alkoxycarbonyl moieties of        C₁-C₆-alkoxycarbonyl-C₁-C₆-alkoxy and        C₁-C₆-alkoxycarbonylamino-C₁-C₄-alkyl: C₁-C₄-alkoxycarbonyl as        mentioned above, and also, for example, pentoxycarbonyl,        1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl,        3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl,        1-ethylpropoxycarbonyl, hexoxycarbonyl,        1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,        1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,        3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,        1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,        1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,        2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,        1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,        1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,        1-ethyl-1-methylpropoxycarbonyl or        1-ethyl-2-methylpropoxycarbonyl;    -   C₁-C₄-alkylthio and also the C₁-C₄-alkylthio moieties of        C₁-C₆-haloalkyl-C₁-C₄-thioalkyl,        C₂-C₆-haloalkenyl-C₁-C₄-thioalkyl,        C₂-C₆-haloalkynyl-C₁-C₄-thioalkyl: for example methylthio,        ethylthio, propylthio, 1-methylethylthio, butylthio,        1-methylpropylthio, 2-methylpropylthio and        1,1-dimethylethylthio;    -   C₁-C₆-alkylthio and also the C₁-C₆-alkylthio moieties of        C₁-C₆-alkylthio-C₁-C₄-alkyl: C₁-C₄-alkylthio as mentioned above,        and also, for example, pentylthio, 1-methylbutylthio,        2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio,        1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio,        1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio,        3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,        1,2-dimethylbutylthio, 1,3-dimethylbutylthio,        2,2-dimethylbutyl-thio, 2,3-dimethylbutylthio,        3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,        1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,        1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;    -   C₁-C₆-alkylamino and also the C₁-C₆-alkylamino radicals of        N—(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl,        C₁-C₆-alkylamino-C₁-C₄-alkyl,        C₁-C₆-alkylsulfonyl(C₁-C₆-alkylamino)-C₁-C₄-alkyl,        C₁-C₆-alkylcarbonyl-(C₁-C₆-alkylamino)-C₁-C₄-alkyl and        [(C₁-C₆-alkyl)amino]cyanoimino: for example methylamino,        ethylamino, propylamino, 1-methylethylamino, butylamino,        1-methylpropylamino, 2-methylpropylamino,        1,1-dimethylethylamino, pentylamino, 1-methylbutylamino,        2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino,        1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino,        1,2-dimethylpropylamino, 1-methylpentylamino,        2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino,        1,1-dimethylbutylamino, 1,2-dimethylbutylamino,        1,3-dimethylbutylamino, 2,2-dimethylbutylamino,        2,3-dimethylbutylamino, 3,3-dimethylbutylamino,        1-ethylbutylamino, 2-ethylbutylamino,        1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino,        1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;    -   di-(C₁-C₄-alkyl)amino: for example N,N-dimethylamino,        N,N-diethylamino, N,N-dipropylamino,        N,N-di-(1-methylethyl)amino, N,N-dibutylamino,        N,N-di-(1-methylpropyl)amino, N,N-di-(2-methylpropyl)amino,        N,N-di-(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,        N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,        N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,        N-methyl-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino,        N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino,        N-ethyl-N-(1-methylpropyl)amino,        N-ethyl-N-(2-methylpropyl)amino,        N-ethyl-N-(1,1-dimethylethyl)amino,        N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,        N-(1-methylpropyl)-N-propylamino,        N-(2-methylpropyl)-N-propylamino,        N-(1,1-dimethylethyl)-N-propylamino,        N-butyl-N-(1-methylethyl)amino,        N-(1-methylethyl)-N-(1-methylpropyl)amino,        N-(1-methylethyl)-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,        N-butyl-N-(1-methylpropyl)amino,        N-butyl-N-(2-methylpropyl)amino,        N-butyl-N-(1,1-dimethylethyl)amino,        N-(1-methylpropyl)-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino and        N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;    -   di(C₁-C₆-alkyl)amino and also the dialkylamino radicals of        N-(di-C₁-C₆-alkylamino)imino-C₁-C₆-alkyl,        di(C₁-C₆-alkyl)amino-C₁-C₄-alkyl,        [di(C₁-C₆-alkyl)aminocarbonyloxy]-C₁-C₄-alkyl,        {di[di(C₁-C₆-alkyl)amino]carbonyloxy}-C₁-C₄-alkyl and        [di(C₁-C₆-alkyl)amino]cyanoimino: di(C₁-C₄-alkyl)amino as        mentioned above, and also, for example, N,N-dipentylamino,        N,N-dihexylamino, N-methyl-N-pentylamino, N-ethyl-N-pentylamino,        N-methyl-N-hexylamino and N-ethyl-N-hexylamino;        (C₁-C₄-alkylamino)carbonyl: for example methylaminocarbonyl,        ethylaminocarbonyl, propylaminocarbonyl,        1-methylethylaminocarbonyl, butylaminocarbonyl,        1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or        1,1-dimethylethylaminocarbonyl;    -   (C₁-C₄-alkylamino)carbonyl and also the        (C₁-C₄-alkylamino)carbonyl moieties of        (C₁-C₄-alkylamino)carbonylamino: for example        methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl,        1-methylethylaminocarbonyl, butylaminocarbonyl,        1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or        1,1-dimethylethylaminocarbonyl;    -   di(C₁-C₄-alkyl)aminocarbonyl and also the        di(C₁-C₄-alkyl)aminocarbonyl moieties of        di(C₁-C₄-alkyl)aminocarbonylamino: for example        N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl,        N,N-di-(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl,        N,N-dibutylaminocarbonyl, N,N-di-(1-methylpropyl)aminocarbonyl,        N,N-di-(2-methylpropyl)aminocarbonyl,        N,N-di-(1,1-dimethylethyl)aminocarbonyl,        N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl,        N-methyl-N-(1-methylethyl)aminocarbonyl,        N-butyl-N-methylaminocarbonyl,        N-methyl-N-(1-methylpropyl)aminocarbonyl,        N-methyl-N-(2-methylpropyl)aminocarbonyl,        N-(1,1-dimethylethyl)-N-methylaminocarbonyl,        N-ethyl-N-propylaminocarbonyl,        N-ethyl-N-(1-methylethyl)aminocarbonyl,        N-butyl-N-ethylaminocarbonyl,        N-ethyl-N-(1-methylpropyl)aminocarbonyl,        N-ethyl-N-(2-methylpropyl)aminocarbonyl,        N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,        N-(1-methylethyl)-N-propylaminocarbonyl,        N-butyl-N-propylaminocarbonyl,        N-(1-methylpropyl)-N-propylaminocarbonyl,        N-(2-methylpropyl)-N-propylaminocarbonyl,        N-(1,1-dimethylethyl)-N-propylaminocarbonyl,        N-butyl-N-(1-methylethyl)aminocarbonyl,        N-(1-methylethyl)N-(1-methylpropyl)aminocarbonyl,        N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,        N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,        N-butyl-N-(1-methylpropyl)aminocarbonyl,        N-butyl-N-(2-methylpropyl)aminocarbonyl,        N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,        N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,        N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or        N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;    -   (C₁-C₆-alkylamino)carbonyl and also the        (C₁-C₆-alkylamino)carbonyl moieties of        (C₁-C₆-alkylamino)carbonylamino,        (C₁-C₆-alkylamino)carbonyloxy-C₁-C₄-alkyl,        C₁-C₆-alkylaminocarbonyl-C₁-C₄-alkyl and        [(C₁-C₆-alkyl)aminocarbonylamino]-C₁-C₄-alkyl:        (C₁-C₄-alkylamino)carbonyl as mentioned above, and also, for        example, pentylaminocarbonyl, 1-methylbutylaminocarbonyl,        2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl,        2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl,        hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl,        1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl,        2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl,        4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl,        1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl,        2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl,        3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl,        2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl,        1,2,2-trimethylpropylaminocarbonyl,        1-ethyl-1-methylpropylaminocarbonyl or        1-ethyl-2-methylpropylaminocarbonyl;    -   di(C₁-C₆-alkyl)aminocarbonyl and also the        di(C₁-C₆-alkyl)aminocarbonyl moieties of        di(C₁-C₆-alkyl)aminocarbonylamino,        di(C₁-C₆-alkyl)aminocarbonyl-C₁-C₄-alkyl and        [di(C₁-C₆-alkyl)aminocarbonylamino]-C₁-C₄-alkyl:        di(C₁-C₄-alkyl)aminocarbonyl as mentioned above, and also, for        example, N-methyl-N-pentylaminocarbonyl,        N-methyl-N-(1-methylbutyl)aminocarbonyl,        N-methyl-N-(2-methylbutyl)aminocarbonyl,        N-methyl-N-(3-methylbutyl)aminocarbonyl,        N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl,        N-methyl-N-(1-ethylpropyl)aminocarbonyl,        N-methyl-N-hexylaminocarbonyl,        N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl,        N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl,        N-methyl-N-(1-methylpentyl)aminocarbonyl,        N-methyl-N-(2-methylpentyl)aminocarbonyl,        N-methyl-N-(3-methylpentyl)aminocarbonyl,        N-methyl-N-(4-methylpentyl)aminocarbonyl,        N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl,        N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl,        N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl,        N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl,        N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl,        N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl,        N-methyl-N-(1-ethylbutyl)aminocarbonyl,        N-methyl-N-(2-ethylbutyl)aminocarbonyl,        N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,        N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,        N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,        N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,        N-ethyl-N-pentylaminocarbonyl,        N-ethyl-N-(1-methylbutyl)aminocarbonyl,        N-ethyl-N-(2-methylbutyl)aminocarbonyl,        N-ethyl-N-(3-methylbutyl)aminocarbonyl,        N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl,        N-ethyl-N-(1-ethylpropyl)aminocarbonyl,        N-ethyl-N-hexylaminocarbonyl,        N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl,        N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl,        N-ethyl-N-(1-methylpentyl)aminocarbonyl,        N-ethyl-N-(2-methylpentyl)aminocarbonyl,        N-ethyl-N-(3-methylpentyl)aminocarbonyl,        N-ethyl-N-(4-methylpentyl)aminocarbonyl,        N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl,        N-ethyl-N-(1-ethylbutyl)aminocarbonyl,        N-ethyl-N-(2-ethylbutyl)aminocarbonyl,        N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,        N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,        N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,        N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,        N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl,        N,N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl,        N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or        N,N-dihexylaminocarbonyl;    -   di(C₁-C₆-alkyl)aminothiocarbonyl: for example        N,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl,        N,N-di-(1-methylethyl)aminothiocarbonyl,        N,N-dipropylaminothiocarbonyl, N,N-dibutylaminothiocarbonyl,        N,N-di-(1-methylpropyl)aminothiocarbonyl,        N,N-di-(2-methylpropyl)aminothiocarbonyl,        N,N-di-(1,1-dimethylethyl)aminothiocarbonyl,        N-ethyl-N-methylaminothiocarbonyl,        N-methyl-N-propylaminothiocarbonyl,        N-methyl-N-(1-methylethyl)aminothiocarbonyl,        N-butyl-N-methylaminothiocarbonyl,        N-methyl-N-(1-methylpropyl)aminothiocarbonyl,        N-methyl-N-(2-methylpropyl)aminothiocarbonyl,        N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl,        N-ethyl-N-propylaminothiocarbonyl,        N-ethyl-N-(1-methylethyl)aminothiocarbonyl,        N-butyl-N-ethylaminothiocarbonyl,        N-ethyl-N-(1-methylpropyl)aminothiocarbonyl,        N-ethyl-N-(2-methylpropyl)aminothiocarbonyl,        N-ethyl-N-(1,1-dimethylethyl)aminothiocarbonyl,        N-(1-methylethyl)-N-propylaminothiocarbonyl,        N-butyl-N-propylaminothiocarbonyl,        N-(1-methylpropyl)-N-propylaminothiocarbonyl,        N-(2-methylpropyl)-N-propylamino-thiocarbonyl,        N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl,        N-butyl-N-(1-methylethyl)aminothiocarbonyl,        N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl,        N-(1-methylethyl)-N-(2-methylpropyl)aminothiocarbonyl,        N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl,        N-butyl-N-(1-methylpropyl)aminothiocarbonyl,        N-butyl-N-(2-methylpropyl)aminothiocarbonyl,        N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl,        N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl,        N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl,        N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl,        N-methyl-N-pentylaminothiocarbonyl,        N-methyl-N-(1-methylbutyl)aminothiocarbonyl,        N-methyl-N-(2-methylbutyl)aminothiocarbonyl,        N-methyl-N-(3-methylbutyl)aminothiocarbonyl,        N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,        N-methyl-N-(1-ethylpropyl)aminothiocarbonyl,        N-methyl-N-hexylaminothiocarbonyl,        N-methyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,        N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,        N-methyl-N-(1-methylpentyl)aminothiocarbonyl,        N-methyl-N-(2-methylpentyl)aminothiocarbonyl,        N-methyl-N-(3-methylpentyl)aminothiocarbonyl,        N-methyl-N-(4-methylpentyl)aminothiocarbonyl,        N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,        N-methyl-N-(1-ethylbutyl)aminothiocarbonyl,        N-methyl-N-(2-ethylbutyl)aminothiocarbonyl,        N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,        N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,        N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,        N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,        N-ethyl-N-pentylaminothiocarbonyl,        N-ethyl-N-(1-methylbutyl)aminothiocarbonyl,        N-ethyl-N-(2-methylbutyl)aminothiocarbonyl,        N-ethyl-N-(3-methylbutyl)aminothiocarbonyl,        N-ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,        N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl,        N-ethyl-N-hexylaminothiocarbonyl,        N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,        N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,        N-ethyl-N-(1-methylpentyl)aminothiocarbonyl,        N-ethyl-N-(2-methylpentyl)aminothiocarbonyl,        N-ethyl-N-(3-methylpentyl)aminothiocarbonyl,        N-ethyl-N-(4-methylpentyl)aminothiocarbonyl,        N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,        N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl,        N-ethyl-N-(2-ethylbutyl)aminothiocarbonyl,        N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,        N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,        N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,        N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,        N-propyl-N-pentylaminothiocarbonyl,        N-butyl-N-pentylaminothiocarbonyl,        N,N-dipentylaminothiocarbonyl,        N-propyl-N-hexylaminothiocarbonyl,        N-butyl-N-hexylaminothiocarbonyl,        N-pentyl-N-hexylaminothiocarbonyl or        N,N-dihexylaminothiocarbonyl;    -   three- to six-membered heterocyclyl and also the three- to        six-membered heterocyclyl moieties of three- to six-membered        heterocyclyl-C₁-C₄-alkyl: monocyclic saturated or partially        unsaturated hydrocarbons having three to six ring members as        mentioned above which, in addition to carbon atoms, may contain        one to four nitrogen atoms or one to three nitrogen atoms and        one oxygen or sulfur atom or one to three oxygen atoms or one to        three sulfur atoms and which may be attached via a carbon atom        or a nitrogen atom,    -   for example 2-oxrianyl, 2-oxetanyl, 3-oxetanyl, 2-aziridinyl,        3-thiethanyl, 1-azetidinyl, 2-azetidinyl,    -   for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl,        2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl,        3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,        5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,        5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl,        5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl,        2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl,        2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl,        1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl,        1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl,        1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl,        1,3,4-triazolidin-2-yl, 1,2,3,4-tetrazolidin-5-yl;    -   for example 1-pyrrolidinyl, 2-isothiazolidinyl,        2-isothiazolidinyl, 1-pyrazolidinyl, 3-oxazolidinyl,        3-thiazolidinyl, 1-imidazolidinyl, 1,2,4-triazolidin-1-yl,        1,2,4-oxadiazolidin-2-yl, 1,2,4-oxadiazolidin-4-yl,        1,2,4-thiadiazolidin-2-yl, 1,2,4-thiadiazolidin-4-yl,        1,2,3,4-tetrazolidin-1-yl,    -   for example 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,        2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,        2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl,        2,4-dihydrothien-3-yl, 4,5-dihydropyrrol-2-yl,        4,5-dihydropyrrol-3-yl, 2,5-dihydropyrrol-2-yl,        2,5-dihydropyrrol-3-yl, 4,5-dihydroisoxazol-3-yl,        2,5-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-3-yl,        4,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-4-yl,        2,3-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl,        2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-5-yl,        4,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-3-yl,        2,3-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl,        2,5-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-4-yl,        4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-5-yl,        2,3-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-2-yl,        2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,        2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-3-yl,        3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl,        4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,        4,5-dihydropyrazol-5-yl, 2,3-dihydroimidazol-2-yl,        2,3-dihydroimidazol-3-yl, 2,3-dihydroimidazol-4-yl,        2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl,        4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl,        2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl,        2,5-dihydroimidazol-5-yl, 2,3-dihydrooxazol-3-yl,        2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl,        3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,        3,4-dihydrooxazol-5-yl, 2,3-dihydrothiazol-3-yl,        2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl,        3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazol-4-yl,        3,4-dihydrothiazol-5-yl, 3,4-dihydrothiazol-2-yl,        3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazol-4-yl,    -   for example 4,5-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl,        4,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-1-yl,        4,5-dihydroisothiazol-1-yl, 2,3-dihydroisothiazol-1-yl,        2,3-dihydropyrazol-1-yl, 4,5-dihydropyrazol-1-yl,        3,4-dihydropyrazol-1-yl, 2,3-dihydroimidazol-1-yl,        4,5-dihydroimidazol-1-yl, 2,5-dihydroimidazol-1-yl,        2,3-dihydrooxazol-2-yl, 3,4-dihydrooxazol-2-yl,        2,3-dihydrothiazol-2-yl, 3,4-dihydrothiazol-2-yl;    -   for example 2-piperidinyl, 3-piperidinyl, 4-piperidinyl,        1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl,        1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-3-yl,        1,3-dithian-4-yl, 1,4-dithian-2-yl, 1,3-dithian-5-yl,        2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl,        2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl,        4-tetrahydrothiopyranyl, 3-hexahydropyridazinyl,        4-hexahydropyridazinyl, 2-hexahydropyrimidinyl,        4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl,        1,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl,        tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-6-yl,        2-morpholinyl, 3-morpholinyl, 1,3,5-trioxan-2-yl;    -   for example 1-piperidinyl, 1-hexahydropyridazinyl,        1-hexahydropyrimidinyl, 1-piperazinyl,        1,3,5-hexahydrotriazin-1-yl, 1,2,4-hexahydrotriazin-1-yl,        tetrahydro-1,3-oxazin-1-yl, 1-morpholinyl;    -   for example 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl,        2H-pyran-5-yl, 2H-pyran-6-yl, 3,6-dihydro-2H-pyran-2-yl,        3,6-dihydro-2H-pyran-3-yl, 3,6-dihydro-2H-pyran-4-yl,        3,6-dihydro-2H-pyran-5-yl, 3,6-dihydro-2H-pyran-6-yl,        3,4-dihydro-2H-pyran-3-yl, 3,4-dihydro-2H-pyran-4-yl,        3,4-dihydro-2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl,        2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl,        5,6-dihydro-4H-1,3-oxazin-2-yl;    -   aryl and the aryl moiety of aryl-(C₁-C₄-alkyl): a monocyclic to        tricyclic aromatic carbocycle having 6 to 14 ring members, such        as, for example, phenyl, naphthyl and anthracenyl;    -   heteroaryl and also the heteroaryl radicals in        heteroaryl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-alkyl,        heteroaryl-C₂-C₄-alkenyl, heteroaryl-C₂-C₄-alkynyl,        heteroaryl-C₁-C₄-halogenalkyl, heteroaryl-C₂-C₄-halogenalkenyl,        heteroaryl-C₂-C₄-halogenalkynyl, heteroaryl-C₁-C₄-hydroxyalkyl,        heteroaryl-C₂-C₄-hydroxyalkenyl,        heteroaryl-C₂-C₄-hydroxyalkynyl, heteroarylcarbonyl-C₁-C₄-alkyl,        heteroarylcarbonyloxy-C₁-C₄-alkyl,        heteroaryloxycarbonyl-C₁-C₄-alkyl, heteroaryloxy-C₁-C₄-alkyl,        heteroarylthio-C₁-C₄-alkyl, heteroarylsulfinyl-C₁-C₄-alkyl,        heteroarylsulfonyl-C₁-C₄-alkyl:    -   mono- or bicyclic aromatic heteroaryl having 5 to 10 ring        members which, in addition to carbon atoms, contains 1 to 4        nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulfur        atom, or an oxygen or a sulfur atom, for example monocycles,        such as furyl (for example 2-furyl, 3-furyl), thienyl (for        example 2-thienyl, 3-thienyl), pyrrolyl (for example        pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (for example pyrazol-3-yl,        pyrazol-4-yl), isoxazolyl (for example isoxazol-3-yl,        isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (for example        isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl        (for example imidazol-2-yl, imidazol-4-yl), oxazolyl (for        example oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (for        example thiazol-2-yl, thiazol-4-yl, thiazol-5-yl), oxadiazolyl        (for example 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl,        1,2,4-oxadiazol-3-yl, 1,2,4,-oxadiazol-5-yl,        1,3,4-oxadiazol-2-yl), thiadiazolyl (for example        1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl,        1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,        1,3,4-thiadiazolyl-2-yl), triazolyl (for example        1,2,3-triazol-4-yl, 1,2,4-triazol-3-yl), tetrazol-5-yl, pyridyl        (for example pyridin-2-yl, pyridin-3-yl, pyridin-4-yl),        pyrazinyl (for example pyridazin-3-yl, pyridazin-4-yl),        pyrimidinyl (for example pyrimidin-2-yl, pyrimidin-4-yl,        pyrimidin-5-yl), pyrazin-2-yl, triazinyl (for example        1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl,        1,2,4-triazin-6-yl), tetrazinyl (for example        1,2,4,5-tetrazin-3-yl); and also bicycles such as the        benzo-fused derivatives of the abovementioned monocycles, for        example quinolinyl, isoquinolinyl, indolyl, benzothienyl,        benzofuranyl, benzoxazolyl, benzothiazolyl, benzisothiazolyl,        benzimidazolyl, benzopyrazolyl, benzothiadiazolyl,        benzotriazolyl.

All phenyl and aryl rings or heterocyclyl and heteroaryl radicals andall phenyl components in phenyl-C₁-C₆-alkyl, phenylcarbonyl,phenylcarbonyl-C₁-C₆-alkyl, phenylcarbonylamino-C₁-C₄-alkyl,phenoxycarbonyl, phenylaminocarbonyl, phenylsulfonylaminocarbonyl,N—(C₁-C₆-alkyl)-N-phenylaminocarbonyl and phenyl-C₁-C₆-alkylcarbonyl,all aryl components in aryl(C₁-C₄-alkyl), all heteroaryl components inmono- or bicyclic heteroaryl and all heterocyclyl components inheterocyclyl-C₁-C₆-alkyl, heterocyclylcarbonyl,heterocyclylcarbonyl-C₁-C₆-alkyl, heterocyclyloxycarbonyl,heterocyclylaminocarbonyl, heterocyclylsulfonylaminocarbonyl,N—(C₁-C₆-alkyl)-N-heterocyclylaminocarbonyl andheterocyclyl-C₁-C₆-alkylcarbonyl are, unless indicated otherwise,preferably unsubstituted or carry one to three halogen atoms and/or onenitro group, one cyano radical and/or one or two methyl,trifluoromethyl, methoxy or trifluoromethoxy substituents.

In a particular embodiment, the variables of the benzoyl-substitutedserineamides of the formula I are as defined below, these definitionsbeing, both on their own and in combination with one another, particularembodiments of the compounds of the formula I:

Preference is given to the benzoyl-substituted serineamides of theformula I in which

-   R¹ is halogen, C₁-C₄-alkyl or C₁-C₆-haloalkyl;    -   particularly preferably halogen or C₁-C₆-haloalkyl;    -   especially preferably halogen or C₁-C₄-haloalkyl;    -   most preferably fluorine, chlorine or CF₃.

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R² and R³ independently of one another are    -   hydrogen, halogen, C₁-C₄-alkyl or C₁-C₆-haloalkyl;    -   very preferably hydrogen, halogen or C₁-C₆-haloalkyl;    -   particularly preferably hydrogen, halogen or C₁-C₄-haloalkyl;    -   especially preferably hydrogen, fluorine, chlorine or CF₃;    -   most preferably hydrogen, fluorine or chlorine;    -   with utmost preference hydrogen or fluorine.

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R⁴ is hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   particularly preferably hydrogen, halogen or C₁-C₄-alkyl;    -   especially preferably hydrogen or halogen;    -   most preferably hydrogen.

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R⁵ is hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;    -   particularly preferably hydrogen, halogen or C₁-C₄-alkyl;    -   especially preferably hydrogen or halogen;    -   most preferably hydrogen.

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R⁶ is hydrogen.

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R⁷ is hydrogen or hydroxyl;    -   particularly preferably hydrogen.

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R⁶ is hydrogen; and-   R⁷ is hydrogen or hydroxyl;    -   particularly preferably hydrogen.

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R⁸ is C₁-C₆-alkyl or C₁-C₆-haloalkyl;    -   particularly preferably C₁-C₆-alkyl;    -   especially preferably C₁-C₄-alkyl;    -   most preferably CH₃.

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R⁹ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, formyl,    C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl,    C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkoxycarbonyl,    C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkylsulfonylaminocarbonyl,    di(C₁-C₆-alkyl)aminocarbonyl,    N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,    di(C₁-C₆-alkyl)aminothiocarbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl,    -   where the alkyl, cycloalkyl and alkoxy radicals mentioned may be        partially or fully halogenated and/or may carry one to three of        the following groups: cyano, hydroxyl, C₃-C₆-cycloalkyl,        C₁-C₄-alkoxy, C₁-C₄-alkylthio, di-(C₁-C₄-alkyl)amino,        C₁-C₄-alkylcarbonyl, hydroxycarbonyl, C₁-C₄-alkoxycarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl,        di-(C₁-C₄-alkyl)aminocarbonyl or C₁-C₄-alkylcarbonyloxy;-    phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl,    phenylcarbonyl-C₁-C₆-alkyl, phenylsulfonylaminocarbonyl or    phenyl-C₁-C₆-alkylcarbonyl,    -   where the phenyl radical may be partially or fully halogenated        and/or may carry one to three of the following groups: nitro,        cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or        C₁-C₄-haloalkoxy; or-    SO₂R¹²;-    particularly preferably hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl,    C₃-C₆-alkynyl, formyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl,    C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylsulfonylaminocarbonyl,    di-(C₁-C₆-alkyl)aminocarbonyl,    N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl or    di-(C₁-C₆-alkyl)aminothiocarbonyl,    -   where the alkyl or alkoxy radicals mentioned may be partially or        fully halogenated and/or may carry one to three of the following        groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkoxycarbonyl,        C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl or        C₁-C₄-alkylcarbonyloxy;-    phenyl-C₁-C₆-alkyl, phenylcarbonyl, phenylcarbonyl-C₁-C₆-alkyl,    phenylsulfonylaminocarbonyl or phenyl-C₁-C₆-alkylcarbonyl,    -   where the phenyl ring may be partially or fully halogenated        and/or may carry one to three of the following groups: nitro,        cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or        C₁-C₄-halooxy; or-    SO₂R¹²;-    especially preferably hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl,    C₃-C₆-alkynyl, formyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl,    C₁-C₆-alkoxycarbonyl, di-(C₁-C₆-alkyl)aminocarbonyl,    N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,    di-(C₁-C₆-alkyl)aminothiocarbonyl, phenyl-C₁-C₆-alkyl,    phenylcarbonyl, phenylcarbonyl-C₁-C₆-alkyl or    phenyl-C₁-C₆-alkylcarbonyl    -   where the phenyl ring may be partially or fully halogenated        and/or may carry one to three of the following groups: nitro,        cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or        C₁-C₄-haloalkoxy; or-    SO₂R¹².

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R⁹ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, formyl,    C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl,    C₃-C₆-cycloalkylcarbonyl, C₁-C₆-alkoxycarbonyl,    C₁-C₆-alkylaminocarbonyl, di-(C₁-C₆-alkyl)aminocarbonyl,    N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,    di-(C₁-C₆-alkyl)aminothiocarbonyl, C₁-C₆-alkoxyimino-C₁-C₆-alkyl,    -   where the alkyl, cycloalkyl or alkoxy radicals mentioned may be        partially or fully halogenated and/or may carry one to three of        the following groups: cyano, hydroxyl, C₃-C₆-cycloalkyl,        C₁-C₄-alkoxy, C₁-C₄-alkylthio, di-(C₁-C₄-alkyl)amino,        C₁-C₄-alkylcarbonyl, hydroxycarbonyl, C₁-C₄-alkoxycarbonyl,        aminocarbonyl, C₁-C₄-alkylaminocarbonyl,        di-(C₁-C₄-alkyl)aminocarbonyl or C₁-C₄-alkylcarbonyloxy; or-    SO₂R¹².

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R⁹ is hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, formyl,    C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl,    di-(C₁-C₆-alkyl)aminocarbonyl,    N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,    -   where the alkyl and alkoxy radicals mentioned may be partially        or fully halogenated and/or may carry one to three of the        following groups: cyano, C₁-C₄-alkoxy, C₁-C₄-alkylaminocarbonyl        or di-(C₁-C₄-alkyl)aminocarbonyl;-    phenyl-C₁-C₆-alkyl, phenylcarbonyl, phenylcarbonyl-C₁-C₆-alkyl,    phenylaminocarbonyl or N—(C₁-C₆-alkyl)-N-(phenyl)aminocarbonyl,    -   where the phenyl ring may be partially or fully halogenated        and/or may carry one to three of the following groups: cyano,        C₁-C₄-alkyl or C₁-C₄-haloalkyl; or-    SO₂R¹²;-   particularly preferably hydrogen, formyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl,    phenylaminocarbonyl, N—(C₁-C₄-alkyl)-N-(phenyl)aminocarbonyl,    SO₂CH₃, SO₂CF₃ or SO₂(C₆H₅).

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R¹⁰ is hydrogen or C₁-C₄-alkyl;    -   preferably hydrogen or CH₃;    -   especially preferably hydrogen.

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-cyanoalkyl,    C₁-C₆-hydroxyalkyl, C₂-C₆-hydroxyalkenyl, C₂-C₆-hydroxyalkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, 3- to 6-membered    heterocyclyl-C₁-C₄-alkyl,    -   where the cycloalkyl, cycloalkenyl or 3- to 6-membered        heterocycyl radicals mentioned above may be partially or fully        halogenated and/or may carry one to three radicals from the        group consisting of oxo, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        hydroxycarbonyl and C₁-C₆-alkoxycarbonyl,-    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-haloalkoxy-C₁-C₄-alkyl,    C₁-C₆-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl,    C₁-C₆-alkylsulfonylamino-C₁-C₄-alkyl, hydroxycarbonyl,    C₁-C₆-alkoxycarbonyl, hydroxycarbonyl-C₁-C₄-alkyl,    C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,    C₁-C₆-haloalkoxycarbonyl-C₁-C₄-alkyl,    C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl,    C₁-C₆-alkylcarbonylamino-C₁-C₄-alkyl,    di(C₁-C₆-alkyl)carbonylamino-C₁-C₄-alkyl,    di(C₁-C₆-alkyl)aminocarbonylamino-C₁-C₄-alkyl,    [(C₁-C₆-alkyl)aminocarbonyl]amino-C₁-C₄-alkyl,    [di(C₁-C₆-alkyl)aminocarbonyloxy]C₁-C₄-alkyl,    {di[di(C₁-C₆-alkyl)amino]carbonyloxy}-C₁-C₄-alkyl,    formylamino-C₁-C₄-alkyl,-    phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl, phenyl-C₂-C₄-alkynyl,    phenyl-C₁-C₄-haloalkyl, phenyl-C₂-C₄-haloalkenyl,    phenyl-C₁-C₄-hydroxyalkyl, phenyloxy-C₁-C₄-alkyl,    phenylthio-C₁-C₄-alkyl, phenylsulfinyl-C₁-C₄-alkyl,    phenylsulfonyl-C₁-C₄-alkyl,-    heteroaryl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-hydroxyalkyl,    heteroaryloxy-C₁-C₄-alkyl, heteroarylthio-C₁-C₄-alkyl,    heteroarylsulfinyl-C₁-C₄-alkyl or heteroarylsulfonyl-C₁-C₄-alkyl,    -   where the phenyl and heteroaryl radicals mentioned above may be        partially or fully halogenated and/or may carry one to three        radicals from the group consisting of cyano, nitro, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, hydroxy, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        hydroxycarbonyl, C₁-C₆-alkoxycarbonyl,        hydroxycarbonyl-C₁-C₆-alkoxy, C₁-C₆-alkylsulfonylamino and        C₁-C₆-haloalkylsulfonylamino;-    particularly preferably C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₁-C₆-hydroxyalkyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-haloalkoxy-C₁-C₄-alkyl,    hydroxycarbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,    C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl,    C₁-C₆-alkylcarbonylamino-C₁-C₄-alkyl,    [di(C₁-C₆-alkyl)aminocarbonyloxy]-C₁-C₄-alkyl,    {di[di(C₁-C₆-alkyl)amino]-carbonyloxy}-C₁-C₄-alkyl,    formylamino-C₁-C₄-alkyl;-    phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl, phenyl-C₂-C₄-alkynyl,    phenyl-C₁-C₄-haloalkyl, phenyl-C₂-C₄-haloalkenyl,    phenyl-C₁-C₄-hydroxyalkyl, phenyloxy-C₁-C₄-alkyl,    phenylthio-C₁-C₄-alkyl, phenylsulfinyl-C₁-C₄-alkyl or    phenylsulfonyl-C₁-C₄-alkyl,    -   where the phenyl radicals mentioned above may be partially or        fully halogenated and/or may carry one to three radicals from        the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, hydroxycarbonyl, C₁-C₆-alkoxycarbonyl,        C₁-C₆-alkylsulfonylamino and C₁-C₆-haloalkylsulfonylamino;-    especially preferably C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₁-C₆-hydroxyalkyl,    hydroxycarbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,    [di(C₁-C₆-alkyl)aminocarbonyloxy]-C₁-C₄-alkyl,    {di[di(C₁-C₆-alkyl)amino]carbonyloxy}-C₁-C₄-alkyl,    formylamino-C₁-C₄-alkyl, formylamino-C₁-C₄-alkyl;-    phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl, phenyl-C₁-C₄-hydroxyalkyl    or phenylthio-C₁-C₄-alkyl;-    most preferably C₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₁-C₆-hydroxyalkyl, hydroxycarbonyl-C₁-C₄-alkyl,    formylamino-C₁-C₄-alkyl, phenyl-C₁-C₄-alkyl or    phenyl-C₁-C₄-hydroxyalkyl.

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-cyanoalkyl,    C₁-C₆-hydroxyalkyl, C₂-C₆-hydroxyalkenyl, C₂-C₆-hydroxyalkinyl,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, 3- to 6-membered heterocyclyl,    -   where the cycloalkyl, cycloalkenyl or 3- to 6-membered        heterocyclyl radicals mentioned above may be partially or fully        halogenated and/or may carry one to three radicals from the        group consisting of oxo, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        hydroxycarbonyl and C₁-C₆-alkoxycarbonyl,-    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-haloalkoxy-C₁-C₄-alkyl,    C₁-C₆-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl,    C₁-C₆-alkylsulfonylamino-C₁-C₄-alkyl, hydroxycarbonyl,    C₁-C₆-alkoxycarbonyl, hydroxycarbonyl-C₁-C₄-alkyl,    C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,    C₁-C₆-haloalkoxycarbonyl-C₁-C₄-alkyl,    C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl,    C₁-C₆-alkylcarbonylamino-C₁-C₄-alkyl,    di(C₁-C₆-alkyl)carbonylamino-C₁-C₄-alkyl,    di(C₁-C₆-alkyl)aminocarbonylamino-C₁-C₄-alkyl,    [(C₁-C₆-alkyl)aminocarbonyl]amino-C₁-C₄-alkyl,    [di(C₁-C₆-alkyl)aminocarbonyloxy]C₁-C₄-alkyl,    formylamino-C₁-C₄-alkyl,-    phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl, phenyl-C₂-C₄-alkynyl,    phenyl-C₁-C₄-haloalkyl, phenyl-C₂-C₄-haloalkenyl,    phenyl-C₁-C₄-hydroxyalkyl, phenyloxy-C₁-C₄-alkyl,    phenylthio-C₁-C₄-alkyl, phenylsulfinyl-C₁-C₄-alkyl,    phenylsulfonyl-C₁-C₄-alkyl,-    heteroaryl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-hydroxyalkyl,    heteroaryloxy-C₁-C₄-alkyl, heteroarylthio-C₁-C₄-alkyl,    heteroarylsulfinyl-C₁-C₄-alkyl or heteroarylsulfonyl-C₁-C₄-alkyl,    -   where the phenyl and heteroaryl radicals mentioned above may be        partially or fully halogenated and/or may carry one to three        radicals from the group consisting of cyano, nitro, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, hydroxy, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        hydroxycarbonyl, C₁-C₆-alkoxycarbonyl,        hydroxycarbonyl-C₁-C₆-alkoxy, C₁-C₆-alkylsulfonylamino and        C₁-C₆-haloalkylsulfonylamino;-    particularly preferably C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₁-C₆-hydroxyalkyl, 3- to    6-membered heterocyclyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,    C₁-C₆-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-haloalkoxy-C₁-C₄-alkyl,    hydroxycarbonyl-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,-    C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl,    C₁-C₆-alkylcarbonylamino-C₁-C₄-alkyl,    [di(C₁-C₆-alkyl)aminocarbonyloxy]C₁-C₄-alkyl,    formylamino-C₁-C₄-alkyl; phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl,    phenyl-C₂-C₄-alkynyl, phenyl-C₁-C₄-haloalkyl,    phenyl-C₂-C₄-haloalkenyl, phenyl-C₁-C₄-hydroxyalkyl,    phenyloxy-C₁-C₄-alkyl, phenylthio-C₁-C₄-alkyl,    phenylsulfinyl-C₁-C₄-alkyl or phenylsulfonyl-C₁-C₄-alkyl,    -   where the phenyl radicals mentioned above may be partially or        fully halogenated and/or may carry one to three radicals from        the group consisting of C₁-C₆-alkyl,        C₁-C₆-haloalkylC₁-C₆-alkoxy, hydroxycarbonyl,        C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylsulfonylamino and        C₁-C₆-haloalkylsulfonylamino;-    especially preferably C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₁-C₆-hydroxyalkyl, 3- to    6-membered heterocyclyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,    C₁-C₆-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxycarbonyl-C₁-C₄-alkyl,    C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,    [di(C₁-C₆-alkyl)aminocarbonyloxy]C₁-C₄-alkyl,    formylamino-C₁-C₄-alkyl;-    phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl, phenyl-C₁-C₄-hydroxyalkyl    or phenylthio-C₁-C₄-alkyl;-    most preferably C₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,    C₁-C₆-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, 3- to 6-membered    heterocyclyl, hydroxycarbonyl-C₁-C₄-alkyl, formylamino-C₁-C₄-alkyl,    phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-hydroxyalkyl.

Preference is likewise given to the benzoyl-substituted serineamides ofthe formula I in which

-   R¹² is C₁-C₆-alkyl, C₁-C₆-haloalkyl or phenyl,    -   where the phenyl radical may be partially or partially        halogenated and/or may be substituted by C₁-C₄-alkyl;-    particularly preferably C₁-C₄-alkyl, C₁-C₄-haloalkyl or phenyl;-    especially preferably methyl, trifluoromethyl or phenyl.

Particular preference is given to the benzoyl-substituted serineamidesof the formula I in which

-   R¹ is fluorine, chlorine or CF₃;-   R² and R³ independently of one another are hydrogen, fluorine or    chlorine;-   R⁴, R⁵, R⁶ and R⁷ are hydrogen;-   R⁸ is C₁-C₄-alkyl,    -   particularly preferably CH₃;-   R⁹ is hydrogen, formyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl,    phenylaminocarbonyl, N—(C₁-C₄-alkyl)-N-(phenyl)aminocarbonyl,    SO₂CH₃, SO₂CF₃ or SO₂(C₆H₅);-   R¹⁰ is hydrogen; and-   R¹¹ C₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,    C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,    C₁-C₆-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, 3- to 6-membered    heterocyclyl, hydroxycarbonyl-C₁-C₄-alkyl, phenyl-C₁-C₄-alkyl or    phenyl-C₁-C₄-hydroxyalkyl.

Most preference is given to the compounds of the formula I.a.(corresponds to formula I where R¹=CF₃, R², R³, R⁴, R⁵, R⁶, R⁷ andR¹⁰=H; R⁸=CH₃), in particular to the compounds of the formulae I.a.1 toI.a.138 of Table 1, where the definitions of the variables R¹ to R¹¹ areof particular importance for the compounds according to the inventionnot only in combination with one another, but in each case also on theirown.

TABLE 1 I.a

No. R⁹ R¹¹ I.a.1 H CH₃ I.a.2 H CH₂CH₃ I.a.3 H CH═CH₂ I.a.4 H CH═CHCH₃I.a.5 H CH═C(CH₃)₂ I.a.6 H C≡CH I.a.7 H CF₃ I.a.8 H CHF₂ I.a.9 H CF₂CF₃I.a.10 H CF₂CHF₂ I.a.11 H CH═CCl₂ I.a.12 H CH═CF₂ I.a.13 H CH₂OH I.a.14H CH₂CH₂OH I.a.15 H CH(OH)CH₂OH I.a.16 H cyclopropyl I.a.17 H cyclohexylI.a.18 H CH₂COOH I.a.19 H CH₂O(CO)CH₃ I.a.20 H CH₂O(CO)N(CH₃)₂ I.a.21 HC≡C(C₆H₅) I.a.22 H CH(OH)CH(OH)C₆H₅ I.a.23 H CH₂S(2-F—C₆H₄) I.a.24C(O)CH₃ CH₃ I.a.25 C(O)CH₃ CH₂CH₃ I.a.26 C(O)CH₃ CH═CH₂ I.a.27 C(O)CH₃CH═CHCH₃ I.a.28 C(O)CH₃ CH═C(CH₃)₂ I.a.29 C(O)CH₃ C≡CH I.a.30 C(O)CH₃CF₃ I.a.31 C(O)CH₃ CHF₂ I.a.32 C(O)CH₃ CF₂CF₃ I.a.33 C(O)CH₃ CF₂CHF₂I.a.34 C(O)CH₃ CH═CCl₂ I.a.35 C(O)CH₃ CH═CF₂ I.a.36 C(O)CH₃ CH₂OH I.a.37C(O)CH₃ CH₂CH₂OH I.a.38 C(O)CH₃ CH(OH)CH₂OH I.a.39 C(O)CH₃ cyclopropylI.a.40 C(O)CH₃ cyclohexyl I.a.41 C(O)CH₃ CH₂COOH I.a.42 C(O)CH₃CH₂O(CO)CH₃ I.a.43 C(O)CH₃ CH₂O(CO)N(CH₃)₂ I.a.44 C(O)CH₃ C≡C(C₆H₅)I.a.45 C(O)CH₃ CH(OH)CH(OH)C₆H₅ I.a.46 C(O)CH₃ CH₂S(2-F—C₆H₄) I.a.47C(O)tertC₄H₉ CH₃ I.a.48 C(O)tertC₄H₉ CH₂CH₃ I.a.49 C(O)tertC₄H₉ CH═CH₂I.a.50 C(O)tertC₄H₉ CH═CHCH₃ I.a.51 C(O)tertC₄H₉ CH═C(CH₃)₂ I.a.52C(O)tertC₄H₉ C≡CH I.a.53 C(O)tertC₄H₉ CF₃ I.a.54 C(O)tertC₄H₉ CHF₂I.a.55 C(O)tertC₄H₉ CF₂CF₃ I.a.56 C(O)tertC₄H₉ CF₂CHF₂ I.a.57C(O)tertC₄H₉ CH═CCl₂ I.a.58 C(O)tertC₄H₉ CH═CF₂ I.a.59 C(O)tertC₄H₉CH₂OH I.a.60 C(O)tertC₄H₉ CH₂CH₂OH I.a.61 C(O)tertC₄H₉ CH(OH)CH₂OHI.a.62 C(O)tertC₄H₉ cyclopropyl I.a.63 C(O)tertC₄H₉ cyclohexyl I.a.64C(O)tertC₄H₉ CH₂COOH I.a.65 C(O)tertC₄H₉ CH₂O(CO)CH₃ I.a.66 C(O)tertC₄H₉CH₂O(CO)N(CH₃)₂ I.a.67 C(O)tertC₄H₉ C≡C(C₆H₅) I.a.68 C(O)tertC₄H₉CH(OH)CH(OH)C₆H₅ I.a.69 C(O)tertC₄H₉ CH₂S(2-F—C₆H₄) I.a.70 C(O)N(CH₃)₂CH₃ I.a.71 C(O)N(CH₃)₂ CH₂CH₃ I.a.72 C(O)N(CH₃)₂ CH═CH₂ I.a.73C(O)N(CH₃)₂ CH═CHCH₃ I.a.74 C(O)N(CH₃)₂ CH═C(CH₃)₂ I.a.75 C(O)N(CH₃)₂C≡CH I.a.76 C(O)N(CH₃)₂ CF₃ I.a.77 C(O)N(CH₃)₂ CHF₂ I.a.78 C(O)N(CH₃)₂CF₂CF₃ I.a.79 C(O)N(CH₃)₂ CF₂CHF₂ I.a.80 C(O)N(CH₃)₂ CH═CCl₂ I.a.81C(O)N(CH₃)₂ CH═CF₂ I.a.82 C(O)N(CH₃)₂ CH₂OH I.a.83 C(O)N(CH₃)₂ CH₂CH₂OHI.a.84 C(O)N(CH₃)₂ CH(OH)CH₂OH I.a.85 C(O)N(CH₃)₂ cyclopropyl I.a.86C(O)N(CH₃)₂ cyclohexyl I.a.87 C(O)N(CH₃)₂ CH₂COOH I.a.88 C(O)N(CH₃)₂CH₂O(CO)CH₃ I.a.89 C(O)N(CH₃)₂ CH₂O(CO)N(CH₃)₂ I.a.90 C(O)N(CH₃)₂C≡C(C₆H₅) I.a.91 C(O)N(CH₃)₂ CH(OH)CH(OH)C₆H₅ I.a.92 C(O)N(CH₃)₂CH₂S(2-F—C₆H₄) I.a.93 C(O)N(CH₃)(C₆H₅) CH₃ I.a.94 C(O)N(CH₃)(C₆H₅)CH₂CH₃ I.a.95 C(O)N(CH₃)(C₆H₅) CH═CH₂ I.a.96 C(O)N(CH₃)(C₆H₅) CH═CHCH₃I.a.97 C(O)N(CH₃)(C₆H₅) CH═C(CH₃)₂ I.a.98 C(O)N(CH₃)(C₆H₅) C≡CH I.a.99C(O)N(CH₃)(C₆H₅) CF₃ I.a.100 C(O)N(CH₃)(C₆H₅) CHF₂ I.a.101C(O)N(CH₃)(C₆H₅) CF₂CF₃ I.a.102 C(O)N(CH₃)(C₆H₅) CF₂CHF₂ I.a.103C(O)N(CH₃)(C₆H₅) CH═CCl₂ I.a.104 C(O)N(CH₃)(C₆H₅) CH═CF₂ I.a.105C(O)N(CH₃)(C₆H₅) CH₂OH I.a.106 C(O)N(CH₃)(C₆H₅) CH₂CH₂OH I.a.107C(O)N(CH₃)(C₆H₅) CH(OH)CH₂OH I.a.108 C(O)N(CH₃)(C₆H₅) cyclopropylI.a.109 C(O)N(CH₃)(C₆H₅) cyclohexyl I.a.110 C(O)N(CH₃)(C₆H₅) CH₂COOHI.a.111 C(O)N(CH₃)(C₆H₅) CH₂O(CO)CH₃ I.a.112 C(O)N(CH₃)(C₆H₅)CH₂O(CO)N(CH₃)₂ I.a.113 C(O)N(CH₃)(C₆H₅) C≡C(C₆H₅) I.a.114C(O)N(CH₃)(C₆H₅) CH(OH)CH(OH)C₆H₅ I.a.115 C(O)N(CH₃)(C₆H₅)CH₂S(2-F—C₆H₄) I.a.116 SO₂CH₃ CH₃ I.a.117 SO₂CH₃ CH₂CH₃ I.a.118 SO₂CH₃CH═CH₂ I.a.119 SO₂CH₃ CH═CHCH₃ I.a.120 SO₂CH₃ CH═C(CH₃)₂ I.a.121 SO₂CH₃C≡CH I.a.122 SO₂CH₃ CF₃ I.a.123 SO₂CH₃ CHF₂ I.a.124 SO₂CH₃ CF₂CF₃I.a.125 SO₂CH₃ CF₂CHF₂ I.a.126 SO₂CH₃ CH═CCl₂ I.a.127 SO₂CH₃ CH═CF₂I.a.128 SO₂CH₃ CH₂OH I.a.129 SO₂CH₃ CH₂CH₂OH I.a.130 SO₂CH₃ CH(OH)CH₂OHI.a.131 SO₂CH₃ cyclopropyl I.a.132 SO₂CH₃ cyclohexyl I.a.133 SO₂CH₃CH₂COOH I.a.134 SO₂CH₃ CH₂O(CO)CH₃ I.a.135 SO₂CH₃ CH₂O(CO)N(CH₃)₂I.a.136 SO₂CH₃ C≡C(C₆H₅) I.a.137 SO₂CH₃ CH(OH)CH(OH)C₆H₅ I.a.138 SO₂CH₃CH₂S(2-F—C₆H₄)

Most preference is likewise given to the compounds of the formula I.b,in particular the compounds of the formulae I.b.1 to I.b.138 whichdiffer from the corresponding compounds of the formulae I.a.1 to I.a.138in that R² is fluorine.

Most preference is likewise given to the compounds of the formula I.c,in particular the compounds of the formulae I.c.1 to I.c.138 whichdiffer from the corresponding compounds of the formulae I.a.1 to I.a.138in that R³ is fluorine.

Most preference is likewise given to the compounds of the formula I.d,in particular the compounds of the formulae I.d.1 to I.d.138 whichdiffer from the corresponding compounds of the formulae I.a.1 to I.a.138in that R⁴ is fluorine.

Most preference is likewise given to the compounds of the formula I.e,in particular the compounds of the formulae I.e.1 to I.e.138 whichdiffer from the corresponding compounds of the formulae I.a.1 to I.a.138in that R² is chlorine.

Most preference is likewise given to the compounds of the formula I.f,in particular the compounds of the formulae I.f.1 to I.f.138 whichdiffer from the corresponding compounds of the formulae I.a.1 to I.a.138in that R³ is chlorine.

Most preference is likewise given to the compounds of the formula I.g,in particular the compounds of the formulae I.g.1 to I.g.138 whichdiffer from the corresponding compounds of the formulae I.a.1 to I.a.138in that R³ and R⁴ are fluorine.

Most preference is likewise given to the compounds of the formula I.h,in particular the compounds of the formulae I.h.1 to I.h.138 whichdiffer from the corresponding compounds of the formulae I.a.1 to I.a.138in that R¹ is chlorine and R² is CF₃.

Most preference is likewise given to the compounds of the formula I.j,in particular the compounds of the formulae I.j.1 to I.j.138 whichdiffer from the corresponding compounds of the formulae I.a.1 to I.a.138in that R¹ and R² are chlorine.

Most preference is likewise given to the compounds of the formula I.k,in particular the compounds of the formulae I.k.1 to I.k.138 whichdiffer from the corresponding compounds of the formulae I.a.1 to I.a.138in that R¹ and R³ are chlorine.

The benzoyl-substituted serineamides of the formula I can be obtained bydifferent routes, for example by the following processes:

Process A

Serine derivatives of the formula V are initially reacted with benzoicacids/benzoic acid derivatives of the formula IV to give thecorresponding benzoyl derivatives of the formula III which are thenreacted with amines of the formula II to give the desiredbenzoyl-substituted serineamides of the formula I:

L¹ is a nucleophilically displaceable leaving group, for examplehydroxyl or C₁-C₆-alkoxy.

L² is a nucleophilically displaceable leaving group, for examplehydroxyl, halogen, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,C₁-C₄-alkylsulfonyl, phosphoryl or isoureyl.

The reaction of the serine derivatives of the formula V with benzoicacids/benzoic acid derivatives of the formula IV where L² is hydroxyl togive benzoyl derivatives of the formula III is carried out in thepresence of an activating reagent and a base, usually at temperatures offrom 0° C. to the boiling point of the reaction mixture, preferably from0° C. to 110° C., particularly preferably at room temperature, in aninert organic solvent [cf. Bergmann, E. D.; et al., J Chem Soc 1951,2673; Zhdankin, V. V.; et al., Tetrahedron Lett. 2000, 41 (28),5299-5302; Martin, S. F. et al., Tetrahedron Lett. 1998, 39 (12),1517-1520; Jursic, B. S. et al., Synth Commun 2001, 31 (4), 555-564;Albrecht, M. et al., Synthesis 2001, (3), 468-472; Yadav, L. D. S. etal., Indian J. Chem B. 41(3), 593-595 (2002); Clark, J. E. et al.,Synthesis (10), 891-894 (1991)].

Suitable activating reagents are condensing agents, such as, forexample, polystyrene-bound dicyclohexylcarbodiimide,diisopropylcarbodiimide, carbonyldiimidazole, chloroformic esters, suchas methyl chloroformate, ethyl chloroformate, isopropyl chloroformate,isobutyl chloroformate, sec-butyl chloroformate or allyl chloroformate,pivaloyl chloride, polyphosphoric acid, propanephosphonic anhydride,bis(2-oxo-3-oxazolidinyl)phosphoryl chloride (BOPCl) or sulfonylchlorides, such as methanesulfonyl chloride, toluenesulfonyl chloride orbenzenesulfonyl chloride.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, suchas benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons, suchas methylene chloride, chloroform, chlorobenzene, ethers, such asdiethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane,anisole and tetrahydrofuran (THF), nitriles, such as acetonitrile andpropionitrile, ketones, such as acetone, methyl ethyl ketone, diethylketone and tert-butyl methyl ketone, and also dimethyl sulfoxide,dimethylformamide (DMF), dimethylacetamide (DMA) and N-methylpyrrolidone(NMP), or else in water; particular preference is given to methylenechloride, THF and water.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, moreover organic bases, for example tertiary amines, suchas trimethylamine, triethylamine, diisopropylethylamine,N-methylmorpholine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Particular preference is given to sodiumhydroxide, triethylamine and pyridine.

The bases are generally employed in equimolar amounts. However, they canalso be used in excess or, if appropriate, as solvent.

Starting materials are generally reacted with one another in equimolaramounts. It may be advantageous to use an excess of IV, based on V.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separating the phases and, if appropriate,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of viscous oilswhich are purified or freed from volatile components under reducedpressure and at moderately elevated temperature. If the intermediatesand end products are obtained as solids, purification can also becarried out by recrystallization or digestion.

The reaction of the serine derivatives of the formula V with benzoicacids/benzoic acid derivatives of the formula IV where L² is halogen,C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₄-alkylsulfonyl,phosphoryl or isoureyl to give benzoyl derivatives of the formula III iscarried out in the presence of a base, usually at temperatures of from0° C. to the boiling point of the reaction mixture, preferably at from0° C. to 100° C., particularly preferably at room temperature, in aninert organic solvent [cf. Bergmann, E. D.; et al., J Chem Soc 1951,2673; Zhdankin, V. V.; et al., Tetrahedron Lett. 2000, 41 (28),5299-5302; Martin, S. F. et al., Tetrahedron Lett. 1998, 39 (12),1517-1520; Jursic, B. S. et al., Synth Commun 2001, 31 (4), 555-564;Albrecht, M. et al., Synthesis 2001, (3), 468-472; Yadav, L. D. S. etal., Indian J. Chem B. 41(3), 593-595 (2002); Clark, J. E. et al.,Synthesis (10), 891-894 (1991)].

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, suchas benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons, suchas methylene chloride, chloroform, chlorobenzene, ethers, such asdiethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane,anisole and tetrahydrofuran (THF), nitriles, such as acetonitrile andpropionitrile, ketones, such as acetone, methyl ethyl ketone, diethylketone and tert-butyl methyl ketone, and also dimethyl sulfoxide,dimethylformamide (DMF), dimethylacetamide (DMA) and N-methylpyrrolidone(NMP), or else in water; particular preference is given to methylenechloride, THF and water.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, moreover organic bases, for example tertiary amines, suchas trimethylamine, triethylamine, diisopropylethylamine,N-methylmorpholine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Particular preference is given to sodiumhydroxide, triethylamine and pyridine.

The bases are generally employed in equimolar amounts. However, they canalso be used in excess or, if appropriate, as solvent.

Starting materials are generally reacted with one another in equimolaramounts. It may be advantageous to use an excess of IV, based on V.

Work-up and isolation of the products can be carried out in a mannerknown per se.

It is, of course, also possible to initially react the serinederivatives of the formula V in an analogous manner with amines of theformula II to give the corresponding amides which are then reacted withbenzoic acids/benzoic acid derivatives of the formula IV to give thedesired benzoyl-substituted serineamides of the formula I.

The serine derivatives of the formula V (for example where L¹=hydroxylor C₁-C₆-alkoxy) required for preparing the benzoyl derivatives of theformula III are known from the literature, even in enantiomerically anddiastereomerically pure form, or they can be prepared in accordance withthe literature cited:

-   -   by condensation of glycine enolate equivalents with aldehydes or        ketones [Blaser, D. et al., Liebigs Ann. Chem. 10, 1067-1078        (1991); Seethaler, T. et al., Liebigs Ann. Chem. 1, 11-17        (1991); Weltenauer, G. et al., Gazz. Chim. Ital. 81, 162 (1951);        Dalla Croce, P. et al., Heterocycles 52(3), 1337-1344 (2000);        Van der Werf, A. W. et al., J. Chem. Soc. Chem. Commun. 100,        682-683 (1991); Caddick, S. et al., Tetrahedron 57 (30),        6615-6626 (2001); Owa, T. et al., Chem. Lett. 1, 83-86 (1988);        Alker, D. et al., Tetrahedron 54 (22), 6089-6098 (1998);        Rousseau, J. F. et al., J. Org. Chem. 63 (8), 2731-2737 (1998);        Saeed, A. et al., Tetrahedron 48 (12), 2507-2514 (1992);        Dong, L. et al., J. Org. Chem. 67 (14), 4759-4770 (2002)].    -   by aminohydroxylation of acrylic acid derivatives [Zhang, H. X.        et al., Tetrahedron Asymmetr. 11 (16), 3439-3447 (2000);        Fokin, V. V. et al., Angew. Chem. Int. Edit. 40(18), 3455        (2001); Sugiyama, H. et al., Tetrahedron Lett. 43(19), 3489-3492        (2002); Bushey, M. L. et al., J. Org. Chem. 64(9), 2984-2985        (1999); Raatz, D. et al., Synlett (12), 1907-1910 (1999)].    -   by nucleophilic substitution of leaving groups in the 2-position        of 3-hydroxypropionic acid derivatives [Owa, T. et al., Chem.        Lett. (11), 1873-1874 (1988); Boger, D. L. et al., J. Org. Chem.        57(16), 4331-4333 (1992); Alcaide, B. et al., Tetrahedron Lett.        36(30), 5417-5420 (1995)].    -   by condensation of aldehydes with nucleophiles with formation of        oxazolines and subsequent hydrolysis [Evans, D. A. et al.,        Angew. Chem. Int. Edit. 40(10), 1884-1888 (2001); Ito, Y. et        al., Tetrahedron Lett. 26(47), 5781-5784 (1985); Togni, A. et        al., J. Organomet. Chem. 381(1), C21-5 (1990); Longmire, J. M.        et al., Organometallics 17(20), 4374-4379 (1998); Suga, H. et        al., J. Org. Chem. 58(26), 7397-7405 (1993)].    -   by oxidative cyclization of 2-acylaminopropionic acid        derivatives to give oxazolines and subsequent hydrolysis        (JP10101655).    -   by Diels-Alder reaction of vinylimines with aldehydes to give        oxazines and subsequent hydrolysis [Bongini, A. et al.,        Tetrahedron Asym. 12(3), 439-454 (2001)].

The benzoic acids/benzoic acid derivatives of the formula IV requiredfor preparing the benzoyl derivatives of the formula III arecommercially available or can be prepared analogously to proceduresknown from the literature from the corresponding halide by a Grignardreaction [for example A. Mannschuk et al., Angew. Chem. 100, 299(1988)].

The reaction of the benzoyl derivatives of the formula III whereL¹=hydroxyl or salts thereof with amines of the formula II to give thedesired benzoyl-substituted serineamides of the formula I is carried outin the presence of an activating reagent and, if appropriate, in thepresence of a base, usually at temperatures of from 0° C. to the boilingpoint of the reaction mixture, preferably at from 0° C. to 100° C.,particularly preferably at room temperature, in an inert organic solvent[cf. Perich, J. W., Johns, R. B., J. Org. Chem. 53 (17), 4103-4105(1988); Somiai, C. et al., Synthesis (3), 285-287 (1992); Gupta, A. etal., J. Chem. Soc. Perkin Trans. 2, 1911 (1990); Guan et al., J. Comb.Chem. 2, 297 (2000)].

Suitable activating reagents are condensing agents, such as, forexample, polystyrene-bound dicyclohexylcarbodiimide,diisopropylcarbodiimide, carbonyldiimidazole, chloroformic esters, suchas methyl chloroformate, ethyl chloroformate, isopropyl chloroformate,isobutyl chloroformate, sec-butyl chloroformate or allyl chloroformate,pivaloyl chloride, polyphosphoric acid, propanephosphonic anhydride,bis(2-oxo-3-oxazolidinyl)phosphoryl chloride (BOPCl) or sulfonylchlorides, such as methanesulfonyl chloride, toluenesulfonyl chloride orbenzenesulfonyl chloride.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, suchas benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons, suchas methylene chloride, chloroform, chlorobenzene, ethers, such asdiethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane,anisole and tetrahydrofuran (THF), nitriles, such as acetonitrile andpropionitrile, ketones, such as acetone, methyl ethyl ketone, diethylketone and tert-butyl methyl ketone, alcohols, such as methanol,ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and alsodimethyl sulfoxide, dimethylformamide (DMF), dimethylacetamide (DMA) andN-methylpyrrolidone (NMP), or else in water; particular preference isgiven to methylene chloride, THF, methanol, ethanol and water.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, moreover organic bases, for example tertiary amines, suchas trimethylamine, triethylamine, diisopropylethylamine,N-methylmorpholine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Particular preference is given to sodiumhydroxide, triethylamine, ethyldiisopropylamine, N-methylmorpholine andpyridine.

The bases are generally employed in catalytic amounts; however, they canalso be employed in equimolar amounts, in excess or, if appropriate, assolvent.

Starting materials are generally reacted with one another in equimolaramounts. It may be advantageous to use an excess of II, based on III.

Work-up and isolation of the products can be carried out in a mannerknown per se.

The reaction of the benzoyl derivatives of the formula III whereL¹=C₁-C₆-alkoxy with amines of the formula II to give the desiredbenzoyl-substituted serineamides of the formula I is usually carried outat temperatures of from 0° C. to the boiling point of the reactionmixture, preferably from 0° C. to 100° C., particularly preferably atroom temperature, in an inert organic solvent, if appropriate in thepresence of a base [cf. Kawahata, N. H. et al., Tetrahedron Lett. 43(40), 7221-7223 (2002); Takahashi, K. et al., J. Org. Chem. 50 (18),3414-3415 (1985); Lee, Y. et al., J. Am. Chem. Soc. 121 (36), 8407-8408(1999)].

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, suchas benzene, toluene, o-, m- and p-xylene, halogenated hydrocarbons, suchas methylene chloride, chloroform, chlorobenzene, ethers, such asdiethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane,anisole and tetrahydrofuran (THF), nitriles, such as acetonitrile andpropionitrile, ketones, such as acetone, methyl ethyl ketone, diethylketone and tert-butyl methyl ketone, alcohols, such as methanol,ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and alsodimethyl sulfoxide, dimethylformamide (DMF), dimethylacetamide (DMA) andN-methylpyrrolidone (NMP), or else in water; particular preference isgiven to methylene chloride, THF, methanol, ethanol and water.

It is also possible to use mixtures of the solvents mentioned.

The reaction may, if appropriate, take place in the presence of a base.Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, moreover organic bases, for example tertiary amines, suchas trimethylamine, triethylamine, diisopropylethylamine,N-methylmorpholine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Particular preference is given to sodiumhydroxide, triethylamine, ethyldiisopropylamine, N-methylmorpholine andpyridine.

The bases are generally employed in catalytic amounts; however, they canalso be employed in equimolar amounts, in excess or, if appropriate, assolvent.

Starting materials are generally reacted with one another in equimolaramounts. It may be advantageous to use an excess of II, based on III.

Work-up and isolation of the products can be carried out in a mannerknown per se.

The amines of the formula II required for preparing thebenzoyl-substituted serineamides of the formula I are commerciallyavailable.

Process B

Benzoyl derivatives of the formula III where R⁹=hydrogen can also beobtained by condensing acylated glycine derivatives of the formula VIIIwhere the acyl group may be a cleavable protective group, such asbenzyloxycarbonyl (cf. VIIIa where Σ=benzyl) or tert-butyloxycarbonyl(cf. VIIIa where Σ=tert-butyl), with carbonyl compounds VII to give thecorresponding aldol products VI. The protective group is then cleavedand the resulting serine derivative of the formula V where R⁹=hydrogenis acylated using benzoic acids/benzoic acid derivatives of the formulaIV.

Analogously, it is also possible to convert an acylated glycinederivative of the formula VIII where the acyl group is a substitutedbenzoyl radical (cf. VIIIb) in the presence of a base with a carbonylcompound VII into the benzoyl derivative III where R⁹=hydrogen:

L¹ is a nucleophilically displaceable leaving group, for examplehydroxyl or C₁-C₆-alkoxy.

L² is a nucleophilically displaceable leaving group, for examplehydroxyl, halogen, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,C₁-C₄-alkylsulfonyl, phosphoryl or isoureyl.

The reaction of the glycine derivatives VIII with carbonyl compounds VIIto give the corresponding aldol product VI or benzoyl derivative IIIwhere R⁹=hydrogen is usually carried out at temperatures of from −100°C. to the boiling point of the reaction mixture, preferably at from −80°C. to 20° C., particularly preferably at from −80° C. to −20° C., in aninert organic solvent in the presence of a base [cf. J.-F. Rousseau etal., J. Org. Chem. 63, 2731-2737 (1998)].

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, suchas toluene, o-, m- and p-xylene, ethers, such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, and also dimethyl sulfoxide, dimethylformamide anddimethylacetamide, particularly preferably diethyl ether, dioxane andtetrahydrofuran.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydrides, such as lithium hydride, sodiumhydride, potassium hydride and calcium hydride, alkali metal azides,such as lithium diisopropylamide, lithium hexamethyldisilazide,organometallic compounds, in particular alkali metal alkyls, such asmethyllithium, butyllithium and phenyllithium, and also alkali metal andalkaline earth metal alkoxides, such as sodium methoxide, sodiumethoxide, potassium ethoxide, potassium tert-butoxide, potassiumtert-pentoxide and dimethoxymagnesium, moreover organic bases, forexample tertiary amines, such as trimethylamine, triethylamine,diisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Particular preference is given to sodium hydride,lithium hexamethyldisilazide and lithium diisopropylamide.

The bases are generally employed in equimolar amounts; however, they canalso be used catalytically, in excess or, if appropriate, as solvents.

The starting materials are generally reacted with one another inequimolar amounts. It may be advantageous to employ an excess of baseand/or carbonyl compounds VII, based on the glycine derivatives VIII.

Work-up and isolation of the products can be carried out in the mannerknown per se.

The glycine derivatives of the formula VIII required for preparing thecompounds I are commercially available, known from the literature [forexample H. Pessoa-Mahana et al., Synth. Comm. 32, 1437 (2002] or can beprepared in accordance with the literature cited.

The protective group is cleaved off by methods known from theliterature, giving serine derivatives of the formula V where R⁹=hydrogen[cf. J.-F. Rousseau et al., J. Org. Chem. 63, 2731-2737 (1998)); J. M.Andres, Tetrahedron 56, 1523 (2000)]; in the case of Σ=benzyl byhydrogenolysis, preferably using hydrogen and Pd/C in methanol; in thecase of Σ=tert-butyl using acid, preferably hydrochloric acid indioxane.

The reaction of the serine derivatives V where R⁹=hydrogen with benzoicacids/benzoic acid derivatives IV to give benzoyl derivatives III whereR⁹=hydrogen is usually carried out analogously to the reaction of theserine derivatives of the formula V with benzoic acids/benzoic acidderivatives of the formula IV to give benzoyl derivatives III mentionedin process A.

Analogously to process A, the benzoyl derivatives of the formula IIIwhere R⁹=hydrogen can then be reacted with amines of the formula II togive the desired benzoyl-substituted serineamides of the formula I whereR⁹=hydrogen which can then be derivatized with compounds of the formulaIX to give benzoyl-substituted serineamides of the formula I [cf., forexample, Yokokawa, F. et al., Tetrahedron Lett. 42 (34), 5903-5908(2001); Arrault, A. et al., Tetrahedron Lett. 43(22), 4041-4044 (2002)].

It is also possible to initially derivatize the benzoyl derivatives ofthe formula III where R⁹=hydrogen with compounds of the formula IX togive further benzoyl derivatives of the formula III [cf., for example,Troast, D. et al., Org. Lett. 4 (6), 991-994 (2002); Ewing W. et al.,Tetrahedron Lett., 30 (29), 3757-3760 (1989); Paulsen, H. et al.,Liebigs Ann. Chem. 565 (1987)], followed by reaction with amines of theformula II analogously to process A, giving the desiredbenzoyl-substituted serineamides of the formula I:

L¹ is a nucleophilically displaceable leaving group, for examplehydroxyl or C₁-C₆-alkoxy.

L³ is a nucleophilically displaceable leaving group, for examplehalogen, hydroxyl, or C₁-C₆-alkoxy.

The reaction of the benzoyl derivatives of the formula III (where, ifappropriate, R⁹=hydrogen) with amines of the formula II to givebenzoyl-substituted serineamides of the formula I (where, ifappropriate, R⁹=hydrogen) is usually carried out analogously to thereaction of the benzoyl derivatives of the formula III with amines ofthe formula II described in process A.

The reaction of the benzoyl derivatives of the formula III whereR⁹=hydrogen or of the benzoyl-substituted serineamides of the formula Iwhere R⁹=hydrogen with compounds of the formula IX to give benzoylderivatives of the formula III or benzoyl-substituted serineamides ofthe formula I is usually carried out at temperatures of from 0° C. to100° C., preferably from 10° C. to 50° C., in an inert organic solventin the presence of a base [cf., for example, Troast, D. et al., Org.Lett. 4 (6), 991-994 (2002); Ewing W. et al., Tetrahedron Lett., 30(29), 3757-3760 (1989); Paulsen, H. et al., Liebigs Ann. Chem. 565(1987)].

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, suchas toluene, o-, m- and p-xylene, halogenated hydrocarbons, such asmethylene chloride, chloroform and chlorobenzene, ethers, such asdiethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane,anisole and tetrahydrofuran, nitriles, such as acetonitrile andpropionitrile, ketones, such as acetone, methyl ethyl ketone, diethylketone and tert-butyl methyl ketone, alcohols, such as methanol,ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and alsodimethyl sulfoxide, dimethylformamide and dimethylacetamide,particularly preferably dichloromethane, tert-butyl methyl ether,dioxane and tetrahydrofuran.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal amides, such as lithium amide,sodium amide and potassium amide, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, organometallic compounds, in particular alkali metalalkyls, such as methyllithium, butyllithium and phenyllithium,alkylmagnesium halides, such as methylmagnesium chloride, and alsoalkali metal and alkaline earth metal alkoxides, such as sodiummethoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide,potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases,for example tertiary amines, such as trimethylamine, triethylamine,diisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Particular preference is given to sodiumhydroxide, sodium hydride and triethylamine.

The bases are generally employed in equimolar amounts; however, they canalso be employed catalytically, in excess or, if appropriate, assolvents.

The starting materials are generally reacted with one another inequimolar amounts. It may be advantageous to use an excess of baseand/or IX, based on III or I.

Work-up and isolation of the products can be carried out in a mannerknown per se.

The required compounds of the formula VIII are commercially available.

Process C

Benzoyl derivatives of the formula III where R⁹=hydrogen can also beobtained by initially acylating aminomalonyl compounds of the formula XIwith benzoic acids/benzoic acid derivatives of the formula IV to givethe corresponding N-acylaminomalonyl compounds of the formula X,followed by condensation with a carbonyl compound of the formula VIIwith decarboxylation:

L¹ is a nucleophilically displaceable leaving group, for examplehydroxyl or C₁-C₆-alkoxy.

L² is a nucleophilically displaceable leaving group, for examplehydroxyl, halogen, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,C₁-C₆-alkylsulfonyl, phosphoryl or isoureyl.

L⁴ is a nucleophilically displaceable leaving group, for examplehydroxyl or C₁-C₆-alkoxy.

The acylation of the aminomalonyl compounds of the formula XI withbenzoic acids/benzoic acid derivatives of the formula IV to give thecorresponding N-acylaminomalonyl compounds of the formula X is usuallycarried out analogously to the reaction, mentioned in process A, of theserine derivatives of the formula V with benzoic acids/benzoic acidderivatives of the formula IV to give the corresponding benzoylderivatives of the formula III.

The reaction of the N-acylaminomalonyl compounds of the formula X withcarbonyl compounds of the formula VIII to give benzoyl derivatives ofthe formula III where R⁹=hydrogen is usually carried out at temperaturesof from 0° C. to 100° C., preferably from 10° C. to 50° C., in an inertorganic solvent in the presence of a base [cf., for example, U.S. Pat.No. 4,904,674; Hellmann, H. et al., Liebigs Ann. Chem. 631, 175-179(1960)].

If L⁴ in the N-acylaminomalonyl compounds of the formula X isC₁-C₆-alkoxy, it is advantageous to initially convert L⁴ by esterhydrolysis [for example Hellmann, H. et al., Liebigs Ann. Chem. 631,175-179 (1960)] into a hydroxyl group.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, suchas toluene, o-, m- and p-xylene, halogenated hydrocarbons, such asmethylene chloride, chloroform and chlorobenzene, ethers, such asdiethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane,anisole and tetrahydrofuran, nitriles, such as acetonitrile andpropionitrile, ketones, such as acetone, methyl ethyl ketone, diethylketone and tert-butyl methyl ketone, alcohols, such as methanol,ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and alsodimethyl sulfoxide, dimethylformamide and dimethylacetamide,particularly preferably diethyl ether, dioxane and tetrahydrofuran.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal amides, such as lithium amide,sodium amide and potassium amide, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, organometallic compounds, in particular alkali metalalkyls, such as methyllithium, butyllithium and phenyllithium,alkylmagnesium halides, such as methylmagnesium chloride, and alsoalkali metal and alkaline earth metal alkoxides, such as sodiummethoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide,potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases,for example tertiary amines, such as trimethylamine, triethylamine,diisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Particular preference is given to triethylamineand diisopropylethylamine.

The bases are generally employed in catalytic amounts; however, they canalso be used in equimolar amounts, in excess or, if appropriate, assolvents.

The starting materials are generally reacted with one another inequimolar amounts. It may be advantageous to employ an excess of base,based on X.

Work-up and isolation of the products can be carried out in a mannerknown per se.

According to the process A or B mentioned above, the resulting benzoylderivatives of the formula III where R⁹=hydrogen can then be convertedinto the desired benzoyl-substituted serineamides of the formula I.

The required aminomalonyl compounds of the formula XI are commerciallyavailable and/or known from the literature [for example U.S. Pat. No.4,904,674; Hellmann, H. et al., Liebigs Ann. Chem. 631, 175-179 (1960)],or they can be prepared in accordance with the literature cited.

The required carbonyl compounds of the formula VII are commerciallyavailable.

Process D

Benzoyl derivatives of the formula III where R⁹ and R¹⁰=hydrogen canalso be obtained by initially acylating keto compounds of the formulaXIII with benzoic acids/benzoic acid derivatives of the formula IV togive the corresponding N-acyl keto compounds of the formula XII,followed by reduction of the keto group [Girard A, Tetrahedron Lett.37(44), 7967-7970 (1996); Nojori R., J. Am. Chem. Soc. 111(25),9134-9135 (1989); Schmidt U., Synthesis (12), 1248-1254 (1992);Bolhofer, A.; J. Am. Chem. Soc. 75, 4469 (1953)]:

L¹ is a nucleophilically displaceable leaving group, for examplehydroxyl or C₁-C₆-alkoxy.

L² is a nucleophilically displaceable leaving group, for examplehydroxyl, halogen, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,C₁-C₆-alkylsulfonyl, phosphoryl or isoureyl.

The acylation of the keto compounds of the formula XIII with benzoicacids/benzoic acid derivatives of the formula IV to give N-acyl ketocompounds of the formula XIII is usually carried out analogously to thereaction, mentioned in process A, of the serine derivatives of theformula V with benzoic acids/benzoic acid derivatives of the formula IVto give the corresponding benzoyl derivatives of the formula III.

The keto compounds of the formula XIII required for preparing thebenzoyl derivatives of the formula III where R⁹ and R¹⁰=hydrogen areknown from the literature [WO 02/083111; Boto, A. et al., TetrahedronLetters 39 (44), 8167-8170 (1988); von Geldern, T. et al., J. of Med.Chem. 39(4), 957-967 (1996); Singh, J. et al., Tetrahedron Letters 34(2), 211-214 (1993); ES 2021557; Maeda, S: et al., Chem. & Pharm. Bull.32 (7), 2536-2543 (1984); Ito, S. et al., J. of Biol. Chem. 256 (15),7834-4783 (1981); Vinograd, L. et al., Zhurnal Organicheskoi Khimii 16(12), 2594-2599 (1980); Castro, A. et al., J. Org. Chem. 35 (8),2815-2816 (1970); JP 02-172956; Suzuki, M. et al., J. Org. Chem. 38(20), 3571-3575 (1973); Suzuki, M. et al, Synthetic Communications 2(4), 237-242 (1972)] or can be prepared according to the literaturecited.

The reduction of the N-acyl keto compounds of the formula XIII tobenzoyl derivatives of the formula III where R⁹ and R¹⁰=hydrogen isusually carried out at temperatures of from 0° C. to 100° C., preferablyfrom 20° C. to 80° C., in an inert organic solvent in the presence of areducing agent.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, suchas toluene, o-, m- and p-xylene, halogenated hydrocarbons, such asmethylene chloride, chloroform and chlorobenzene, ethers, such asdiethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane,anisole and tetrahydrofuran, nitrites, such as acetonitrile andpropionitrile, ketones, such as acetone, methyl ethyl ketone, diethylketone and tert-butyl methyl ketone, alcohols, such as methanol,ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and alsodimethyl sulfoxide, dimethyl formamide and dimethyl acetamide,particularly preferably toluene, methylene chloride or tert-butyl methylether.

It is also possible to use mixtures of the solvents mentioned.

Suitable reducing agents are, for example, sodium borohydride, zincborohydride, sodium cyanoborohydride, lithium triethylborohydride(Superhydrid®), lithium tri-sec-butylborohydride (L-Selectrid®)),lithium aluminum hydride or borane [cf., for example, WO 00/20424;Marchi, C. et al., Tetrahedron 58 (28), 5699 (2002); Blank, S. et al.,Liebigs Ann. Chem. (8), 889-896 (1993); Kuwano, R. et al., J. Org. Chem.63 (10), 3499-3503 (1998); Clariana, J. et al., Tetrahedron 55 (23),7331-7344 (1999)].

Furthermore, the reduction can also be carried out in the presence ofhydrogen and a catalyst. Suitable catalysts are, for example,[Ru(BINAP)Cl₂] or Pd/C [cf. Noyori, R. et al., J. Am. Chem. Soc. 111(25), 9134-9135 (1989); Bolhofer, A. et al., J. Am. Chem. Soc. 75, 4469(1953)].

In addition, the reduction can also be carried out in the presence of amicroorganism. A suitable microorganism is, for example, Saccharomycesrouxii [cf. Soukup, M. et al., Helv. Chim. Acta 70, 232 (1987)].

The N-acyl keto compounds of the formula XII and the reducing agent inquestion are generally reacted with one another in equimolar amounts. Itmay be advantageous to employ an excess of reducing agent, based on XII.

Work-up and isolation of the products can be carried out in the mannerknown per se.

The resulting benzoyl derivatives of the formula III where R⁹ andR¹⁰=hydrogen can then, according to the processes A and B mentionedabove, be converted into the desired benzoyl-substituted serineamides ofthe formula I.

Process E

Benzoyl derivatives of the formula III where R⁹=hydrogen andR¹¹=—C(OH)R′R″ can also be obtained by dihydroxylating vinylglycines ofthe formula XIV with an oxidizing agent such as osmium tetroxide orpermanganate:

L¹ is a nucleophilically displaceable leaving group, for examplehydroxyl or C₁-C₆-alkoxy.

R′ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, phenylor C₁-C₆-alkoxycarbonyl.

R″ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, phenylor C₁-C₆-alkoxycarbonyl.

This reaction is usually carried out at temperatures of from −78° C. tothe boiling point of the reaction mixture, preferably from −10° C. to120° C., particularly preferably from 0° C. to 50° C., in an inertorganic solvent, if appropriate in the presence of a reoxidizing agent,such as, for example, N-methylmorpholine N-oxide (D. Johnson et al.,Tetrahedron 2000, 56, 5, 781).

Suitable solvents are halogenated hydrocarbons, such as methylenechloride, chloroform and chlorobenzene, ethers, such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles, such as acetonitrile and propionitrile,ketones, such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone,

alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanoland tert.-butanol, and also dimethyl sulfoxide, dimethylformamide,dimethylacetamide and water; particularly preferably acetone or water.

It is also possible to use mixtures of the solvents mentioned.

The starting materials are generally reacted with one another inequimolar amounts. It may be advantageous to employ an excess ofoxidizing agent, based on XIV.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separation of the phases and, if required,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of viscous oilswhich are purified or freed from volatile components under reducedpressure and at moderately elevated temperature. If the intermediatesand end products are obtained as solids, purification may also be byrecrystallization or digestion.

The vinylglycines of the formula XIV required for preparing the benzoylderivatives of the formula III where R⁹=hydrogen and R¹¹=—C(OH)R′R″ areknown from the literature [D. B. Berkowitz et al., J. Org. Chem. 2000,65, 10, 2907; M. Koen et al., J. Chem. Soc. Perkin I 1997, 4, 487] orcan be prepared in accordance to the literature cited.

Analogously to process A, the benzoyl derivatives of the formula IIIwhere R⁹=hydrogen and R¹¹=—C(OH)R′R″ can then be reacted with amines ofthe formula II to give the desired benzoyl-substituted serineamides ofthe formula I where R⁹=hydrogen and R¹¹=—C(OH)R′R″, which can then bederivatized with compounds of the formula IX to give benzoyl-substitutedserineamides of the formula I where R″=—C(OR⁹)R′R″ [cf., for example,Yokokawa, F. et al., Tetrahedron Lett. 42 (34), 5903-5908 (2001);Arrault, A. et al., Tetrahedron Lett. 43(22), 4041-4044 (2002)];

also, the benzoyl derivatives of the formula III where R⁹=hydrogen caninitially be derivatized analogously to process B with compounds of theformula IX to give further benzoyl derivatives of the formula III whereR¹¹=—C(OR⁹)R′R″ [cf., for example, Troast, D. et al., Org. Lett. 4 (6),991-994 (2002); Ewing W. et al., Tetrahedron Lett., 30 (29), 3757-3760(1989); Paulsen, H. et al., Liebigs Ann. Chem. 565 (1987)] and then bereacted analogously to process A with amines of the formula II to givethe desired benzoyl-substituted serineamiden of the formula I whereR″=—C(OR⁹)R′R″:

L¹ is a nucleophilically displaceable leaving group, for examplehydroxyl or C₁-C₆-alkoxy.

L³ is a nucleophilically displaceable leaving group, for examplehalogen, hydroxyl or C₁-C₆-alkoxy.

R′ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, phenylor C₁-C₆-alkoxycarbonyl.

R″ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, phenylor C₁-C₆-alkoxycarbonyl.

Process F

Benzoyl derivatives of the formula III where R⁹=hydrogen andR¹¹=—C(Nuc)R′R″ can also be obtained by epoxidizing vinylglycines of theformula XIV with an epoxidizing agent to give epoxyglycines of theformula XV, followed by nucleophilic opening of the epoxide:

L¹ is a nucleophilically displaceable leaving group, for examplehydroxyl or C₁-C₆-alkoxy.

R′ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, phenylor C₁-C₆-alkoxycarbonyl.

R″ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, phenylor C₁-C₆-alkoxycarbonyl.

Nuc⁻M⁺ is, for example, a thiolate, such as, for example, sodiumthiophenolate, an alcoxide, such as potassium phenoxide, or an amide,such as sodium imidazolate.

The epoxidation is usually carried out at temperatures of from −78° C.to the boiling point of the reaction mixture, preferably from −20° C. to50° C., in particular from 0° C. to 30° C., in an inert organic solvent[cf. P. Meffre et al., Tetrahedron Lett. 1990, 31, 16, 2291].

Suitable epoxidizing agents are peracids and peroxides (for examplemetachloroperbenzoic acid, peracetic acid, dimethyldioxirane, hydrogenperoxide).

Suitable solvents are halogenated hydrocarbons, such as methylenechloride, chloroform and chlorobenzene, alcohols, such as methanol,ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and alsowater, particularly preferably halogenated hydrocarbons and water.

It is also possible to use mixtures of the solvents mentioned.

The starting materials are generally reacted with one another inequimolar amounts. It may be advantageous to employ an excess ofepoxidizing agent, based on XIV.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separation of the phases and, if required,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of viscous oilswhich are purified or freed from volatile components under reducedpressure and at moderately elevated temperature. If the intermediatesand end products are obtained as solids, purification may also be byrecrystallization or digestion.

The vinylglycines of the formula XIV required for preparing the benzoylderivatives of the formula III where R⁹=hydrogen and R¹¹=—C(OH)R′R″ areknown from the literature [D. B. Berkowitz et al., J. Org. Chem. 2000,65, 10, 2907; M. Koen et al., J. Chem. Soc. Perkin I 1997, 4, 487] orcan be prepared in accordance with the literature cited.

The opening of the epoxide is usually carried out at temperatures offrom −78° C. to the boiling point of the reaction mixture, preferablyfrom −20° C. to 100° C., particularly preferably from 0° C. to 50° C.,in an inert organic solvent, if appropriate in the presence of acatalyst [cf. P. Meffre et al., Tetrahedron Lett. 1990, 31, 16, 2291; M.R. Paleo et al., J. Org. Chem. 2003, 68, 1, 130].

Suitable solvents are alcohols, such as methanol, ethanol, n-propanol,isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide,dimethylformamide and dimethylacetamide and water, particularlypreferably methanol and water.

It is also possible to use mixtures of the solvents mentioned.

Suitable acid catalysts are Lewis acids, such as boron trifluoride,aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV)chloride, zinc(II) chloride and magnesium perchlorate.

The catalyst is usually employed in an amount of from 1 to 100 mol %,preferably from 1 to 10 mol %, based on the compound XV.

The starting materials are generally reacted with one another inequimolar amounts. It may be advantageous to employ an excess of Nuc⁻M⁺,based on XV.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separation of the phases and, if required,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of viscous oilswhich are purified or freed from volatile components under reducedpressure and at moderately elevated temperature. If the intermediatesand end products are obtained as solids, purification may also be byrecrystallization or digestion.

Analogously to process A, the benzoyl derivatives of the formula IIIwhere R⁹=hydrogen and R¹¹=—C(Nuc)R′R″ can then be reacted with amines ofthe formula II to give the desired benzoyl-substituted serineamides ofthe formula I where R⁹=hydrogen and R¹¹=—C(Nuc)R′R″, which can then bederivatized with compounds of the formula IX to give benzoyl-substitutedserineamides of the formula I where R¹¹=—C(OR⁹)R′R″ [cf., for example,Yokokawa, F. et al., Tetrahedron Lett. 42 (34), 5903-5908 (2001);Arrault, A. et al., Tetrahedron Lett. 43(22), 40414044 (2002)];

also, the benzoyl derivatives of the formula III where R⁹=hydrogen caninitially be derivatized analogously to process B with compounds of theformula IX to give further benzoyl derivatives of the formula III whereR¹¹=—C(Nuc)R′R″ [cf., for example, Troast, D. et al., Org. Lett. 4 (6),991-994 (2002); Ewing W. et al., Tetrahedron Lett., 30 (29), 3757-3760(1989); Paulsen, H. et al., Liebigs Ann. Chem. 565 (1987)] and then bereacted analogously to process A with amines of the formula II to givethe desired benzoyl-substituted serineamiden of the formula I whereR¹¹=—C(Nuc)R′R″:

L¹ is a nucleophilically displaceable leaving group, for examplehydroxyl or C₁-C₆-alkoxy.

L³ is a nucleophilically displaceable leaving group, for examplehalogen, hydroxyl or C₁-C₆-alkoxy.

R′ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, phenylor C₁-C₆-alkoxycarbonyl.

R″ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-hydroxyalkyl, phenylor C₁-C₆-alkoxycarbonyl.

Nuc⁻M⁺ is, for example, a thiolate, such as, for example, sodiumthiophenolate, an alcoxide, such as potassium phenoxide, or an amide,such as sodium imidazolate.

The present invention also provides benzoyl derivatives of the formulaIII

where R¹ to R⁶ and R⁹ to R¹¹ are as defined above and L¹ is hydroxyl orC₁-C₆-alkoxy.

The particularly preferred embodiments of the intermediates with respectto the variables correspond to those of the radicals R¹ to R⁶ and R⁹ toR¹¹ of the formula I.

Particular preference is given to benzoyl derivatives of the formula IIIin which

-   R¹ is fluorine, chlorine or CF₃;-   R² and R³ independently of one another are hydrogen, fluorine or    chlorine;-   R⁴, R⁵ and R⁶ are hydrogen;-   R⁹ is hydrogen, formyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-alkylaminocarbonyl, di-(C₁-C₄-alkyl)-aminocarbonyl,    phenylaminocarbonyl, N—(C₁-C₄-alkyl)-N-(phenyl)aminocarbonyl,    SO₂CH₃, SO₂CF₃ or SO₂(C₆H₅);-   R¹⁰ is hydrogen; and-   R¹¹ is C₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₁-C₆-hydroxyalkyl, hydroxycarbonyl-C₁-C₄-alkyl,    phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-hydroxyalkyl.

The examples below serve to illustrate the invention.

PREPARATION EXAMPLES Example 14-(3-Fluorophenylsulfanyl)-2-(4-fluoro-2-trifluoromethylbenzoylamino)-3-hydroxy-N-methylbutyramide(Tab. 3, No. 3.12) 1.1)4-Fluoro-N-(1-hydroxymethyl-allyl)-2-trifluoromethylbenzamide

19 g (146 mmol) of 2-S-2-aminobut-3-en-1-ol hydrochloride were suspendedin CH₂Cl₂ and 59 g (584 mmol) of triethylamine and 68.2 g of4-fluoro-2-trifluoromethylbenzoyl chloride were successively addeddropwise at 0° C. The mixture was then stirred at RT for 15 h. Thesolvent was removed and the residue was taken up in ethyl acetate andstirred with 5% strength NaHCO₃ solution. The insoluble residue was thenfiltered off and the filtrate was re-extracted with 5% strength NaHCO₃.The organic phase was concentrated and the residue (65.8 g) wasdissolved in THF. At 0° C., 7.3 g (300 mmol) of LiOH in H₂O were addeddropwise to the solution. The solution was stirred at RT for 15 h, thesolvents were then removed and the residue was extracted with CH₂Cl₂.The combined organic phases were washed and dried, and the solvent wasthen removed. This gave 34.8 g (86% of theory) of the title compound asa colorless solid.

¹H-NMR (DMSO): δ=3.4-3.6 (m, 2H); 4.50 (t, 1H); 4.85 (t, 1H); 5.15 (d,1H); 5.25 (d, 1H); 5.8-6.0 (m, 1H); 7.5-7.7 (m, 3H); 8.55 (d, 1H).

1.2) 2-(4-Fluoro-2-trifluoromethylbenzoylamino)but-3-enoic acid

At RT, 51.5 g (226 mmol) of periodic acid and 9.9 g (99 mmol) of CrO₃were dissolved in acetonitrile/water. Furthermore, 25 g (90.3 mmol) of4-fluoro-N-(1-hydroxymethylallyl)-2-trifluoromethylbenzamide weredissolved in acetonitrile/water and the NalO₄/CrO₃ solution which hadbeen prepared earlier was added dropwise at 0-5° C. over a period of 3h. The mixture was then stirred at RT for 15 h. 400 ml of 6% strengthNa₂HPO₄ solution were then added dropwise, toluene and ethyl acetatewere added and the phases were separated. The aqueous phase wasre-extracted with ethyl acetate. The combined organic phases werewashed, dried and concentrated. This gave 24.1 g (92% of theory) of thetitle compound.

¹H-NMR (DMSO): δ=5.00 (t, 1H); 5.30 (d, 1H); 5.40 (d, 1H); 5.9-6.1 (m,1H); 7.5-7.7 (m, 3H); 9.10 (d, 1H); 13.0 (br, 1H).

1.3) Methyl 2-(4-fluoro-2-trifluoromethylbenzoylamino)-but-3-enoate

25 g (90.3 mmol) of2-(4-fluoro-2-trifluoromethylbenzoylamino)but-3-enoic acid weredissolved in methanol, and 9.9 g (82.8 mmol) of thionyl chloride wereadded dropwise over a period of 30 min. The solution was stirred at RTfor three days. Removal of the solvent gave 25.2 g of product (100% oftheory) of the title compound as a colorless solid.

¹H-NMR (DMSO): δ=3.70 (s, 3H); 5.05 (t, 1H); 5.30 (d, 1H); 5.40 (d, 1H);5.9-6.0 (m, 1H); 7.5-7.7 (m, 3H); 9.30 (d, 1H).

1.4) Methyl (4-fluoro-2-trifluoromethyl-benzoylamino)oxiranylacetate

16.0 g (52.5 mmol) of methyl2-(4-fluoro-2-trifluoromethylbenzoylamino)but-3-enoate were dissolved inCH₂Cl₂, 14.1 g (63.0 mmol) of 70% strength m-chloroperbenzoic acid(MCPBA) were added and the mixture was stirred at RT for 15 h. Thesolvents were then removed and the residue was purifiedchromatographically.

This gave a mixture of starting material and product which was stirredwith 6 g (26.8 mmol) of MCPBA in CH₂Cl₂ for another 60 h. Analogouswork-up and chromatography gave 7 g (42% of theory) of diasteromericallypure title compound as a colorless solid, and also 2.5 g of startingmaterial.

¹H-NMR (DMSO): δ=2.70 (m, 1H); 2.85 (t, 1H); 3.40 (m, 1H); 3.70 (s, 3H);4.45 (t, 1H); 7.55-7.75 (m, 3H); 9.25 (d, 1H).

1.5) Methyl4-(3-fluorophenylsulfanyl)-2-(4-fluoro-2-trifluoromethylbenzoylamino)-3-hydroxybutyrate(Tab. 2. No. 2.7)

480 mg (1.5 mmol) of methyl(4-fluoro-2-trifluoromethylbenzoylamino)oxiranylacetate were dissolvedin methanol, and 215 mg (1.5 mmol) of 3-fluorothiophenol and 280 mg (3.8mmol) of triethylamine were then added. The mixture was then stirred atRT for 15 h, and the solvent was then removed. This gave 760 mg ofdiasteromerically pure crude product which was used for the next stepwithout further purification.

¹H-NMR (DMSO): δ=3.15 (d, 2H); 3.70 (s, 3H); 4.65 (m, 1H); 4.85 (d, 1H);5.65 (d, 1H); 7.0-7.4 (m, 4H); 7.6-7.8 (m, 3H); 8.85 (d, 1H).

1.6)4-(3-Fluorophenylsulfanyl)-2-(4-fluoro-2-trifluoromethylbenzoylamino)-3-hydroxy-N-methylbutyramide(Tab. 3, No. 3.12)

760 mg (about 1.5 mmol) of crude product from step 1.5 were dissolved inmethanol. With gentle cooling, gaseous methylamine was then introducedfor 30 min. The mixture was stirred at RT for 15 h. The solvents werethen removed, the residue was stirred with MTBE and the precipitate wasfiltered off with suction. This gave 416 mg (62% of theory over 2 steps)of the title compound (4:1 diastereomer mixture) as a colorless solid ofm.p. 172° C.

¹H-NMR (DMSO, main diastereomer): δ=2.65 (d, 3H); 3.0-3.2 (m, 2H); 4.05(m, 1H); 4.65 (dd, 1H); 5.55 (d, 1H); 6.9-7.4 (m, 4H); 7.6-8.8 (m, 4H);8.45 (d, 1H).

Example 22-Dimethylcarbamoyloxy-3-(4-fluoro-2-trifluoromethylbenzoylamino)-3-methylcarbamoylpropylN,N-dimethylcarbamate (Tab. 3, No. 3.56) 2.1) Methyl2-(4-fluoro-2-trifluoromethylbenzoylamino)-3,4-dihydroxybutyrate (Tab.2, No. 2.8)

460 mg (1.5 mmol) of methyl2-(4-fluoro-2-trifluoromethylbenzoylamino)but-3-enoate were dissolved intert-butanol/water, and 360 mg (3 mmol) of N-methylmorpholine N-oxideand 1.5 g (0.15 mmol) of a 2.5% strength solution of OsO₄ intert-butanol were added. The mixture was stirred at RT for 60 hours. 3.2g of sodium sulfite, water and ethyl acetate were then added, and thephases were separated. The aqueous phase was reextracted with ethylacetate. The combined organic phases were washed and dried, and thesolvent was removed. This gave 440 mg (86% of theory) of crude product(diastereomer ratio about 2:1) which was used for the next step withoutfurther purification.

2.2)2-(4-Fluoro-2-trifluoromethylbenzoylamino)-3,4-dihydroxy-N-methylbutyramide(Tab. 3, No. 3.8)

650 mg (1.5 mmol) of crude product from 2.1. above were dissolved inmethanol, and with gentle cooling gaseous methylamine was introduced for30 min. The mixture was stirred at RT for 15 h. The solvents were thenremoved, the residue was stirred with MTBE and the precipitate wasfiltered off with suction. This gave 340 mg (67% of theory over 2 steps)of the title compound as a colorless solid (diasteromer ratio 2:1) ofm.p. 163° C.

¹H-NMR (DMSO, main diastereomer): δ=2.65 (d, 3H); 3.4-3.6 (m, 2H); 3.90(m, 1H); 4.50 (d, 1H); 4.60 (m, 1H); 5.05 (m, 1H); 7.6-7.8 (m, 4H); 8.15(d, 1H).

2.3)2-Dimethylcarbamoyloxy-3-(4-fluoro-2-trifluoromethylbenzoylamino)-3-methylcarbamoylpropylN,N-dimethylcarbamate (Tab. 3, No. 3.54)

170 mg (0.5 mmol) of2-(4-fluoro-2-trifluoromethylbenzoylamino)-3,4-dihydroxy-N-methylbutyramidewere dissolved in 550 mg (5.0 mmol) of dimethylcarbamoyl chloride and150 mg (1.5 mmol) of triethylamine. 10 mg of dimethylaminopyridine wereadded, and the reaction mixture was heated at 50° C. for 18 h. Duringthis period, three times a further 200 mg of dimethylcarbamoyl chlorideand 50 mg of triethylamine were added in each case. The reaction mixturewas then concentrated, taken up in ethyl acetate, washed, dried andreconcentrated. This gave 140 mg (58% of theory) of the title compoundas a colorless solid (diastereomer ratio 4:1) of m.p. 64° C.

¹H-NMR (DMSO, main diastereomer): δ=2.65 (d, 3H); 2.80 (s, 6H); 3.00 (s,3H); 3.10 (s, 3H); 4.0-4.2 (m, 3H), 4.7-4.8 (m, 1H); 7.6-7.8 (m, 3H);8.85 (d, 1H).

Example 3N-(2-Hydroxy-1-methylcarbamoylbut-3-enyl)-4-fluoro-2-trifluoromethylbenzamide(Tab. 3, No. 3.3) 3.1) Ethyl(4-fluoro-2-trifluoromethylbenzoylamino)acetate

30.7 g (0.22 mol) of ethyl glycinate hydrochloride were suspended inCH₂Cl₂. At 0° C., 86.3 g (0.854 mol) of triethylamin and 50 g (0.22 mol)of 2-trifluoromethyl-4-fluorobenzoylchlorid dissolved in 250 ml ofCH₂Cl₂ were successively added dropwise. After 48 h at RT, the solutionwas washed and dried, and the solvent was removed. This gave 62.2 g (97%of theory) of the title compound as a colorless solid.

¹H-NMR (DMSO): δ=1.2 (t, 3H); 4.00 (d, 2H); 4.15 (q, 2H); 7.6-7.8 (m,3H); 9.00 (t, 1H).

3.2) Ethyl3-hydroxy-2-(4-fluoro-2-trifluoromethylbenzoylamino)pent-4-enoate (Tab.2, No. 2.6)

At −78° C., 6.0 g (0.0205 mol) of ethyl(4-fluoro-2-trifluoromethylbenzoylamino)acetate dissolved in THF wereadded dropwise to 24.3 ml (0.049 mol) of a 2M lithium diisopropylamidesolution in THF. After 1 h at −78° C., 1.4 g (0.025 mol) of acroleindissolved in THF were added dropwise, and the mixture was stirred at−78° C. for 1 h. Saturated NH₄Cl solution was then added, and themixture was allowed to warm to RT. The mixture was extracted withCH₂Cl₂, and the combined organic phases were then washed and dried andthe solvent was removed. The residue was purified chromtographically(SiO₂; cyclohexane/ethyl acetate). This gave 4.7 g (66% of theory) ofthe title compound as a colorless solid (diastereomer mixture) which wasreacted further without further purification.

3.3)N-(2-Hydroxy-1-methylcarbamoylbut-3-enyl)-4-fluoro-2-trifluoromethylbenzamide(Tab. 3, No. 3.3)

4.5 g (12.9 mmol) of ethyl3-hydroxy-2-(4-fluoro-2-trifluoromethylbenzoylamino)pent-4-enoate weredissolved in methanol. With ice cooling methylamine gas was introducedfor 2 h. The reaction solution was then concentrated and washed. Thisgave 3.1 g (80% of theory) of the title compound as a colorless solid(diastereomer ratio 2:1).

¹H-NMR (main diastereomer): δ=2.60 (d, 3H); 4.25 (br, 1H); 4.35 (t, 1H);5.15 (d, 1H); 5.30 (d, 1H); 5.35 (d, 1H); 5.85 (m, 1H); 7.5-7.8 (m, 3H);7.90 (d, 1H); 8.65 (d, 1H).

Example 42-Chloro-1-[(4-fluoro-2-trifluoromethylbenzoylamino)methylcarbamoylmethyl]-3-phenylallylN,N-dimethylcarbamate (Tab. 3, No. 3.53) 4.1.) Ethyl4-chloro-3-hydroxy-5-phenyl-2-(4-fluoro-2-trifluoromethylbenzoylamino)pent-4-enoate(Tab. 2, No. 2.6)

At −75° C., 5.0 g (0.0170 mol) of ethyl(4-fluoro-2-trifluoromethylbenzoylamino)acetate dissolved in THF wereadded dropwise to 25.0 ml (0.050 mol) of a 2M solution of lithiumdiisopropylamide in THF. After 1 h at −75° C., 3.50 g (0.021 mol) of2-chlorocinnamaldehyde dissolved in THF were added dropwise, and themixture was stirred at −75° C. for 1 h. Saturated NH₄Cl solution wasadded dropwise and the mixture was warmed to RT and extracted withCH₂Cl₂. The combined organic phases were washed and dried, and thesolvent was removed. The residue was purified chromatographically (SiO₂,cyclohexane/ethyl acetate). This gave 7.5 g (96% of theory) of the titlecompound as a colorless solid (diastereomer mixture) which was reactedfurther without further purification.

4.2)N-(3-Chloro-2-hydroxy-1-methylcarbamoyl-4-phenylbut-3-enyl)-4-fluoro-2-trifluoromethylbenzamide(Tab. 3, No. 3.6)

7.8 g (16.9 mmol) of ethyl4-chloro-3-hydroxy-5-phenyl-2-(4-fluoro-2-trifluoromethylbenzoylamino)pent-4-enoatewere dissolved in methanol. With ice cooling, methylamine gas wasintroduced for 3 h. The reaction solution was then concentrated, washedwith pentane and recrystallized from acetone. The residue gave 1.2 g oftarget product as a pure diastereomer. The filtrate was concentrated,which afforded 7.0 g of a diastereomer mixture. Accordingly, this gave atotal of 1.9 g (100% of theory) of the title compound as a colorlesssolid of m.p 140° C.

¹H-NMR (DMSO) (Rückstand): δ=2.65 (d, 3H); 4.60 (m, 1H); 4.65 (t, 1H);5.95 (d, 1H); 6.85 (s, 1H); 7.2-7.8 (m, 8H); 8.10 (d, 1H); 8.75 (d, 1H).

4.3)2-Chloro-1-[(4-fluoro-2-trifluoromethylbenzoylamino)methylcarbamoylmethyl]-3-phenylallylN,N-dimethylcarbamate (Tab. 3, No. 3.53)

400 mg (0.90 mmol) ofN-(3-chloro-2-hydroxy-1-methylcarbamoyl-4-phenylbut-3-enyl)-4-fluoro-2-trifluoromethylbenzamide,2.36 g (22.0 mmol) of dimethylaminocarbonyl chloride, 1.81 g (17.8 mmol)of triethylamine and about 10 ml of dimethylaminopyridine were dissolvedin dioxane and heated under reflux for 6 h. The reaction solution wasthen concentrated, the residue was taken up in CH₂Cl₂ and washed and thesolvent was removed. The residue was washed with pentane/diisopropylether and dried. This gave 0.30 g (65% of theory) of the title compoundas a colorless solid of m.p. 210° C.

¹H-NMR (DMSO): δ=2.70 (s, 3H); 2.80 (s, 3H); 2.90 (s, 3H); 5.00 (t, 1H);5.55 (d, 1H); 6.95 (s, 1H); 7.3-7.8 (m, 8H); 8.45 (m, 1H); 9.00 (s, 1H).

Example 54-Fluoro-N-(3,3,3-trifluoro-2-hydroxy-1-methylcarbamoylpropyl)-2-trifluoromethylbenzamide(Tab. 3, No. 3.1) 5.1) Ethyl4,4,4-trifluoro-2-(4-fluoro-2-trifluoromethylbenzoylamino)-3-hydroxybutyrate(Tab. 2, No. 2.1)

1.7 g (8.5 mmol) of ethyl 2-amino-4,4,4-trifluoro-3-hydroxybutyrate weredissolved in THF, and initially 1.8 g of4-fluoro-2-trifluoromethylbenzoic acid and 2.6 g (25.4 mmol) oftriethylamine and then, at 5° C., 1.9 g (8.5 mmol) ofbis(2-oxo-3-oxazolinidylphosphoryl chloride were added. The mixture wasstirred at RT for 16 h. The reaction solution was then concentrated, andthe residue was diluted with water and extracted with ethyl acetate. Thecombined organic phases were dried and the solvent was removed. Thisgave 3.1 g (93% of theory) of the title compound as a colorless residue.

¹H-NMR (DMSO): δ=1.20 (t, 3H); 4.20 (m, 2H); 4.65 (m, 1H); 5.05 (q, 1H);6.95 (d, 1H); 7.4-7.8 (m, 3H); 9.05 (d, 1H).

5.2.)4-Fluoro-N-(3,3,3-trifluoro-2-hydroxy-1-methylcarbamoylpropyl)-2-trifluoromethylbenzamide(Tab. 3, No. 3.1)

3.1 g (7.9 mmol) of ethyl4,4,4-trifluoro-2-(4-fluoro-2-trifluoromethylbenzoylamino)-3-hydroxybutyratewere dissolved in ethanol. At RT, 20 ml of a 3.9% strength solution ofmethylamine in ethanol was added. After 5 h of stirring at RT,methylamine gas was introduced for 10 min and the mixture was stirred atRT for 16 h. The reaction solution was then concentrated, and theresidue was washed with MTBE. This gave 1.8 g (61% of theory) of thetitle compound as colorless crystals (diastereomer ratio 3:1) of m.p.212° C.

¹H-NMR (DMSO) (main diastereoisomer): δ=2.65 (d, 3H); 4.50 (br, 1H);4.80 (d, 1H); 6.80 (br, 1H); 7.6-7.8 (m, 3H); 7.85 (br, 1H); 8.55 (d,1H).

In addition to the above compounds, further benzoyl derivatives of theformula III and benzoyl-substituted serineamides of the formula I whichwere prepared or are preparable in a manner analogously to the processesdescribed above are listed in Tables 2, 3 and 4 below.

TABLE 2 III

No. R⁹ R¹¹ L¹ Ratio of diastereomers Chirality M+ (m/z) 2.1. H CF₃ OC₂H₅3:1 rac 391 2.2. H CH═CH₂ OC₂H₅ 1:1 rac 349 2.3. H CH═C(CH₃)₂ OC₂H₅ 1:1rac 377 2.4. H CH═C(CH₃)₂ OC₂H₅ 1:0 rac 377 2.5. H C(CH₃)═CHCH₃ (anti)OC₂H₅ 1:2 rac 377 2.6. H CCl═CH(C₆H₅) (syn) OC₂H₅ 1:0 rac 459 2.7. HCH₂OH OCH₃ 1:0 2-S 339 2.8. H —CH₂—S-(3-F-phenyl) OCH₃ 1:0 2.S 449

TABLE 3 I

Ratio of M+ No. R⁹ R¹¹ distereomers Chirality M.p. (m/z) 3.1. H CF₃ 3:1rac 212 3.2. H CF₂CHF₂ 0:1 rac 210 408 3.3. H CH═CH₂ 1:1 rac 163 3343.4. H CH═C(CH₃)₂ 1:1 rac 125 362 3.5. H CH═C(CH₃)₂ 1:0 rac 169 362 3.6.H C(CH₃)═CHCH₃ (anti) 1:2 rac 115 362 3.7. H CCl═CH(C₆H₅) (syn) 1:0 rac140 444 3.8. H CH₂OH 2:1 2-S 163 338 3.9. H CH(OH)CH(OH)(C₆H₅) 3:2 rac97 414 3.10. H CH₂—S—(C₆H₅) 1:0 2-S 157 3.11. H CH₂—S-(2-F-phenyl) 4:12-S 151 3.12. H CH₂—S-(3-F-phenyl) 4:1 2-S 172 3.13. HCH₂—S-(2-Cl-phenyl) 8:1 2-S 161 3.14. H CH₂—S-(2-CH₃-phenyl) 4:1 2-S 1433.15. H CH₂—S-(1-imidazolyl) 4:1 2-S 171 3.16. H CH₂—S-(2-imidazolyl)4:1 2-S 159 3.17. H CH₂—S-[2-(4,6-OCH₃)-pyrimidyl] 6:1 2-S 209 3.18. HCH₂—SO₂—(C₆H₅) 3.19. H CH₂—SO₂-(2-F-phenyl) 8:1 2-S 128 3.20. HCH₂—SO₂-(3-F-phenyl) 4:1 2-S 131 3.21. H CH₂—SO₂-(2-Cl-phenyl) 8:1 2-S165 3.22. H CH₂—SO₂-(2-CH₃-phenyl) 4:1 2-S 132 3.23. HCH₂—SO₂-[2-(4,6-OCH₃)-pyrimidyl] 4:1 2-S 164 3.24. CH₂(C₆H₅) CH₃ 1:0 2-S412 3.25. Si(CH₂CH₃)₃ CF₃ 5:1 rac 128 490 3.26. (CO)CH₃ CF₃ 7:3 rac 182418 3.27. (CO)CH₃ CF₂CHF₂ 4.1 rac 155 450 3.28. (CO)CH₃ CH═CH₂ 3:1 rac137 376 3.29. (CO)CH₃ CH═C(CH₃)₂ 1:0 rac 170 3.30. (CO)C(CH₃)₃ CF₃ 1:0rac 196 3.31. (CO)C(CH₃)₃ CF₂CHF₂ 1:0 rac 156 492 3.32. (CO)CH₂OCH₃ CF₃2:1 rac 163 448 3.33. (CO)CH₂OCH₃ CF₂CHF₂ 4:1 rac 151 480 3.34.(CO)CH₂OCH₂CH₂OCH₃ CF₃ 1:1 rac 144 492 3.35. (CO)CH₂OCH₂CH₂OCH₃ CF₂CHF₂4:1 rac 134 524 3.36. (CO)CH₂O(2,4-Cl₂—C₆H₃) CF₃ 4:1 rac 204 579 3.37.(CO)CH₂O(2,4-Cl₂—C₆H₃) CF₂CHF₂ 4:1 rac 137 611 3.38. (CO)CH₂SCH₃ CF₃ 2:1rac 161 464 3.39. (CO)CH₂SCH₃ CF₂CHF₂ 4:1 rac 165 496 3.40. (CO)CH₂SC₆H₅CF₃ 2:1 rac 154 526 3.41. (CO)CH₂SC₆H₅ CF₂CHF₂ 4:1 rac 137 558 3.42.(CO)CH₂S[2-(4,6-OCH₃)pyrimidyl] CF₂CHF₂ 4:1 rac 170 620 3.43. (CO)CH₂NH₃⁺ Cl⁻ CF₃ 2:1 rac 193 3.44. (CO)CH₂NH(CO)OC(CH₃)₃ CF₃ 4:1 rac 109 5333.45. (CO)CH₂NH(CO)OC(CH₃)₃ CF₂CHF₂ 4:1 rac 164 565 3.46. (CO)N(CH₃)₂CHC(CH₃)₂ 1:0 rac 197 3.47. (CO)N(CH₃)₂ CH(OH)CH₂OH 2:1 rac 140 4393.48. (CO)N(CH₃)₂ [1,3]-dioxolan-2-on-4-yl 2:1 rac ¹* 465 3.49.(CO)N(CH₃)₂ CF₃ 2:1 rac 447 3.50. (CO)N(CH₃)₂ CF₂CHF₂ 1:0 rac 170 4793.51. (CO)N(CH₃)₂ CF₂CHF₂ 0:1 rac 211 479 3.52. (CO)N(CH₃)₂ CH═CH₂ 3:1rac 128 405 3.53. (CO)N(CH₃)₂ CCl═CH(C₆H₅) (syn) 1:0 rac 210 515 3.54.(CO)N(CH₃)₂ CH₂O(CO)N(CH₃)₂ 1:0 2-S  64 3.55. (CO)N(CH₃)₂CH[OCON(CH₃)₂][phenyl] 2:1 rac 578 3.56. (CO)N(CH₃)₂CH[O(CO)N(CH₃)₂][CH₂O(CO)N(CH₃)₂] 2:1 rac 135 3.57. (CO)N(CH₃)₂CH₂—S-(2-F-phenyl) 4:1 2-S 519 3.58. (CO)N(CH₃)₂ CH₂—S-(3-F-phenyl) 4:12-S 519 3.59. (CO)N(CH₃)₂ CH₂—S-(2-Cl-phenyl) 4:1 2-S 535 3.60.(CO)N(CH₃)₂ CH₂—S-[2-(4,6-OCH₃)-pyrimidyl] 4:1 2-S ²* 3.61. O(CO)CH₃CH═CH₂ 3:1 rac 137 376 3.62. O(CO)CH₃ CH═C(CH₃)₂ 1:1 rac 170 404¹*¹H-NMR (d4-MeOH): δ = 2.75 (2 + d, 3 H); 2.9 (br, 6 H); 4.6-4.8 (m, 3H); 5.0-5.4 (m, 2 H); 7.4-7.6 (m, 3 H) ²*¹H-NMR (d4-MeOH): δ = 2.75 (s,3 H); 3.05 (s, 3 H); 3.20 (s, 3 H); 3.4-3.6 (m, 2 H); 3.95 (s, 6 H);5.00 (d, 1 H); 5.50 (q, 1 H); 5.85 (s, 1 H); 7.4-7.6 (m, 3 H)

TABLE 4 I

Ratio of M+ No. R¹ R² R³ R⁹ R¹¹ diastereomers Chirality M.p. (m/z) 4.1.CF₃ H H H CH═CH₂ 1:0 rac 316 4.2. CF₃ H H H CH(OH)CH(OH)(C₆H₅) 3:2 rac75 396 4.3. CF₃ H H CH₂(C₆H₅) CH₃ 1:0 2-S 394 4.4. CF₃ H H (CO)N(CH₃)₂CH═CH₂ 1.0 rac 142 387 4.5. CF₃ H H O(CO)CH₃ CH═CH₂ 1:0 rac 146 4.6. ClCl H H CH(OH)CH(OH)(C₆H₅) 3:2 rac 397 4.7. Cl H H CH₂(C₆H₅) CH₃ 1:0 2-S395 4.8. Cl H Cl CH₂(C₆H₅) CH₃ 1:0 2-S 395 4.9. Cl CF₃ H HCH(OH)CH(OH)(C₆H₅) 1:1 rac 128 431 4.10. Cl CF₃ H CH₂(C₆H₅) CH₃ 1:0 2-S428

TABLE 5 I

Ratio of M+ No. R³ R⁹ R¹¹ diastereomers Chirality M.p. (m/z) 5.1. H(CH₃)₂NCO CH≡C(CH₃)₂ 3:2 rac. 132 5.2. H (CH₃)₂NCO CH₂OHCH₂OH 4:1 rac.421 5.3. H (CH₃)₂NCO cyclopropyl 0:1 rac. 188 5.4. H CH₃CO CH═C(CH₃)₂3:2 rac. 165 5.5. H CH₃HNCO CH═C(CH₃)₂ 4:1 rac. 143 5.6. H H CH═C(CH₃)₂3:2 rac. 175 5.7. H H CH═C(CH₃)₂ 3:1 rac. 169 5.8. F (CH₃)₂NCO2-(CONHCH₃)-cyclopropyl 1:1 rac. 233 5.9. F (CH₃)₂NCO2-(COOC₂H₅)-cyclopropyl 0:1 rac. 195 5.10. F (CH₃)₂NCO2-(COOH)-cyclopropyl 0:1 rac. 194 5.11. F (CH₃)₂NCO3-(2H-tetrahydrothiopyranyl) 0:1 rac. 212 5.12. F (CH₃)₂NCO3-(2H-tetrahydrothiopyranyl sulfoxide) 0:1 rac. 215 5.13. F (CH₃)₂NCO3-2H-tetrahydropyranyl 1:0 rac. 463 5.14. F (CH₃)₂NCO3-2H-tetrahydropyranyl 2:1 rac. 162 5.15. F (CH₃)₂NCO3-2H-tetrahydropyranyl 4:1 rac. 190 5.16. F (CH₃)₂NCO CH₂(C₆H₅) 0:1 rac.228 5.17. F (CH₃)₂NCO CH₂CH₂(C₆H₅) 1:1 rac. 483 5.18. F (CH₃)₂NCOCH₂CH₂COOH 1:1 rac. 176 5.19. F (CH₃)₂NCO CH₂CH₂SCH₃ 1:1 rac. 148 5.20.F (CH₃)₂NCO CH₂CH₂SO₂CH₃ 1:1 rac. 175 5.21. F (CH₃)₂NCO CH₂CH₂SOCH₃ 1:1rac. 469 5.22. F (CH₃)₂NCO CH₂NH₃ ⁺Cl⁻ 4:1 rac. 180 5.23. F (CH₃)₂NCOCH₂NHCO(2-F—C₆H₄) 7:3 rac. 149 5.24. F (CH₃)₂NCO CH₂NHCOCH₂OCH₃ 7:3 rac. 45 5.25. F (CH₃)₂NCO CH₂NHCOCH₃ 4:1 rac. 176 5.26. F (CH₃)₂NCO CH₂NHCOH7:3 rac. 105 5.27. F (CH₃)₂NCO CH₂NHCON(CH₃)₂ 3:2 rac. 207 5.28. F(CH₃)₂NCO CH₂NHCONHCH₃ 1:0 rac. 465 5.29. F (CH₃)₂NCO CH₂NHCOOC(CH₃)₃5:1 rac. 193 5.30. F (CH₃)₂NCO CH₂SCH₃ 0:1 rac. 214 5.31. F (CH₃)₂NCOCH₂SCH₃ 1:0 rac. 156 5.32. F (CH₃)₂NCO CH₂SO₂CH₃ 1:9 rac. 238 5.33. F(CH₃)₂NCO CH₂SO₂CH₃ 1:0 rac. 180 5.34. F (CH₃)₂NCO CH₂SOCH₃ 1:9 rac. 1715.35. F (CH₃)₂NCO CH₂SOCH₃ 1:0 rac. 150 5.36. F (CH₃)₂NCOcis-CH═CH(C₆H₅) 3:2 rac. 481 5.37. F (CH₃)₂NCO cyclohexyl 0:1 rac. 2115.38. F (CH₃)₂NCO cyclopentyl 0:1 rac. 154 5.39. F (CH₃)₂NCO cyclopentyl3:2 rac.  45 5.40. F (CH₃)₂NCO cyclopropyl 1:1 rac. 211 5.41. F(CH₃)₂NCO cyclopropyl 1:1 rac. 189 5.42. F CH₃CO 2-(CONHCH₃)-cyclopropyl1:1 rac. 235 5.43. F CH₃CO CH₂(C₆H₅) 0:1 rac. 208 5.44. F CH₃COCH₂CH₂(C₆H₅) 1:0 rac. 454 5.45. F CH₃CO CH₂CH₂(C₆H₅) 0:1 rac. 180 5.46.F CH₃CO CH₂CH₂COOH 1:0 rac. 197 5.47. F CH₃CO CH₂COOH 0:1 rac. 212 5.48.F CH₃CO CH₂NHCOCH₃ 1:1 rac. 197 5.49. F CH₃CO CH₂SCH₃ 0:1 rac. 166 5.50.F CH₃CO CH₂SCH₃ 7:3 rac. 170 5.51. F CH₃CO CH₂SO₂CH₃ 0:1 rac. 229 5.52.F CH₃CO CH₂SO₂CH₃ 7:3 rac. 198 5.53. F CH₃CO CH₂SOCH₃ 0:1 rac. 196 5.54.F CH₃CO CH₂SOCH₃ 7:3 rac. 183 5.55. F CH₃CO cyclohexyl 0:1 rac. 1865.56. F CH₃CO cyclopentyl 3:2 rac. 186 5.57. F CH₃CO cyclopropyl - 0:1rac. 205 5.58. F CH₃CO cyclopropyl 1:1 rac. 180 5.59. F CH₃HNCO2-(CONHCH₃)-cyclopropyl 1:1 rac. 199 5.60. F CH₃HNCO3-2H-tetrahydropyranyl 1:1 rac. 195 5.61. F CH₃HNCO CH═C(CH₃)₂ 3:1 rac.182 5.62. F CH₃HNCO cyclohexyl 1:4 rac. 202 5.63. F CH₃HNCO cyclopentyl0:1 rac. 184 5.64. F CH₃HNCO cyclopentyl 3:2 rac. 205 5.65. F CH₃HNCOcyclopropyl 1:1 rac. 220 5.66. F CH₃HNCO cyclopropyl 0:1 rac. 234 5.67.F H 2-(CONHCH₃)-cyclopropyl 1:1 rac. 235 5.68. F H2-(COOC₂H₅)-cyclopropyl 0:1 rac. 420 5.69. F H3-(2H-tetrahydrothiopyranyl) 0:1 rac. 207 5.70. F H3-2H-tetrahydropyranyl 5:1 rac. 191 5.71. F H 3-2H-tetrahydropyranyl 1:1rac.  87 5.72. F H 4-2H-tetrahydropyranyl 1:1 rac. 207 5.73. F HCH₂(C₆H₅) 0:1 rac. 187 5.74. F H CH₂CH₂(C₆H₅) 0:1 rac. 209 5.75. F HCH₂CH₂SCH₃ 1:1 rac. 191 5.76. F H CH₂NH₃ ⁺Cl⁻ 1:1 rac. 188 5.77. F HCH₂NHCOCH₃ 3:2 rac. 211 5.78. F H CH₂NHCON(CH₃)₂ 0:1 rac. 408 5.79. F HCH₂NHCON(CH₃)₂ 1:0 rac. 408 5.80. F H CH₂NHCOOC(CH₃)₃ 1:1 rac. 144 5.81.F H CH₂NHCOOC(CH₃)₃ 1:0 rac. 155 5.82. F H CH₂NHSO₂CF₃ 2:1 rac. 1875.83. F H CH₂SCH₃ 1:9 rac. 209 5.84. F H CH₂SCH₃ 7:3 rac. 179 5.85. F Hcyclohexyl 1:3 rac. 166 5.86. F H cyclopentyl 0:1 rac. 214 5.87. F Hcyclopentyl 2:3 rac. 175 5.88. F H cyclopropyl 0:1 rac. 348 5.89. F Hcyclopropyl 1:1 rac. 199

Biological Activity

The benzoyl-substituted serineamides of the formula I and theiragriculturally useful salts are suitable, both in the form of isomermixtures and in the form of the pure isomers, as herbicides. Theherbicidal compositions comprising compounds of the formula I controlvegetation on non-crop areas very efficiently, especially at high ratesof application. They act against broad-leaved weeds and grass weeds incrops such as wheat, rice, maize, soya and cotton without causing anysignificant damage to the crop plants. This effect is mainly observed atlow rates of application.

Depending on the application method in question, the compounds of theformula I, or herbicidal compositions comprising them, can additionallybe employed in a further number of crop plants for eliminatingundesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica),Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I may also be used in cropswhich tolerate the action of herbicides owing to breeding, includinggenetic engineering methods.

In addition, the compounds of the formula I may also be used in cropswhich tolerate attack by fungi or insects owing to breeding, includinggenetic engineering methods.

The compounds of the formula I, or the herbicidal compositionscomprising them, can be used for example in the form of ready-to-sprayaqueous solutions, powders, suspensions, also highly concentratedaqueous, oily or other suspensions or dispersions, emulsions, oildispersions, pastes, dusts, materials for broadcasting, or granules, bymeans of spraying, atomizing, dusting, spreading or watering. The useforms depend on the intended purpose; in any case, they should ensurethe finest possible distribution of the active ingredients according tothe invention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or an agriculturally useful saltof 1, and auxiliaries which are customary for the formulation of cropprotection agents.

Suitable as inert auxiliaries are essentially the following:

mineral oil fractions of medium to high boiling point, such as keroseneand diesel oil, furthermore coal tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, for exampleparaffin, tetrahydronaphthalene, alkylated naphthalenes and theirderivatives, alkylated benzenes and their derivatives, alcohols such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, strongly polar solvents, for example amines such asN-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubstrates, either as such or dissolved in an oil or solvent, can behomogenized in water by means of a wetting agent, tackifier, dispersantor emulsifier. Alternatively, it is also possible to prepareconcentrates comprising active substance, wetting agent, tackifier,dispersant or emulsifier and, if desired, solvent or oil, which aresuitable for dilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkalineearth metal salts and ammonium salts of aromatic sulfonic acids, forexample ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonicacid, and of fatty acids, alkyl- and alkylarylsulfonates, alkylsulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts ofsulfated hexa-, hepta- and octadecanols, and also of fatty alcoholglycol ethers, condensates of sulfonated naphthalene and its derivativeswith formaldehyde, condensates of naphthalene or of thenaphthalenesulfonic acids with phenol and formaldehyde, polyoxyethyleneoctylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol,alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyetheralcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignosulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixingor grinding the active ingredients together with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogeneous granules, can be prepared by binding the active ingredientsto solid carriers. Solid carriers are mineral earths such as silicas,silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole,loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesiumsulfate and magnesium oxide, ground synthetic materials, fertilizerssuch as ammonium sulfate, ammonium phosphate, ammonium nitrate andureas, and products of vegetable origin, such as cereal meal, tree barkmeal, wood meal and nutshell meal, cellulose powders, or other solidcarriers.

The concentrations of the compounds of the formula I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise approximately from 0.001 to 98% by weight,preferably 0.01 to 95% by weight of at least one active ingredient. Theactive ingredients are employed in a purity of from 90% to 100%,preferably 95% to 100% (according to NMR spectrum).

The formulation examples below illustrate the preparation of suchpreparations:

-   I. 20 parts by weight of an active compound of the formula I are    dissolved in a mixture composed of 80 parts by weight of alkylated    benzene, 10 parts by weight of the adduct of from 8 to 10 mol of    ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by    weight of calcium dodecylbenzenesulfonate and 5 parts by weight of    the adduct of 40 mol of ethylene oxide to 1 mol of castor oil.    Pouring the solution into 100 000 parts by weight of water and    finely distributing it therein gives an aqueous dispersion which    comprises 0.02% by weight of the active ingredient of formula I.-   II. 20 parts by weight of an active compound of the formula I are    dissolved in a mixture composed of 40 parts by weight of    cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight    of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol    and 10 parts by weight of the adduct of 40 mol of ethylene oxide to    1 mol of castor oil. Pouring the solution into 100 000 parts by    weight of water and finely distributing it therein gives an aqueous    dispersion which comprises 0.02% by weight of the active ingredient    of formula I.-   III. 20 parts by weight of an active compound of the formula I are    dissolved in a mixture composed of 25 parts by weight of    cyclohexanone, 65 parts by weight of a mineral oil fraction of    boiling point 210 to 280° C. and 10 parts by weight of the adduct of    40 mol of ethylene oxide to 1 mol of castor oil. Pouring the    solution into 100 000 parts by weight of water and finely    distributing it therein gives an aqueous dispersion which comprises    0.02% by weight of the active ingredient of formula I.-   IV. 20 parts by weight of an active compound of the formula I are    mixed thoroughly with 3 parts by weight of sodium    diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium    salt of a lignosulfonic acid from a sulfite waste liquor and 60    parts by weight of pulverulent silica gel, and the mixture is ground    in a hammer mill. Finely distributing the mixture in 20 000 parts by    weight of water gives a spray mixture which comprises 0.1% by weight    of the active ingredient of formula I.-   V. 3 parts by weight of an active compound of the formula I are    mixed with 97 parts by weight of finely divided kaolin. This gives a    dust which comprises 3% by weight of the active ingredient of    formula I.-   VI. 20 parts by weight of an active compound of the formula I are    mixed intimately with 2 parts by weight of calcium    dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol    polyglycol ether, 2 parts by weight of the sodium salt of a    phenol/urea/formaldehyde condensate and 68 parts by weight of a    paraffinic mineral oil. This gives a stable oily dispersion.-   VII. 1 part by weight of an active compound of the formula I is    dissolved in a mixture composed of 70 parts by weight of    cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and    10 parts by weight of ethoxylated castor oil. This gives a stable    emulsion concentrate.-   VIII. 1 part by weight of an active compound of the formula I is    dissolved in a mixture composed of 80 parts by weight of    cyclohexanone and 20 parts by weight of Wettol® EM 31 (=nonionic    emulsifier based on ethoxylated castor oil). This gives a stable    emulsion concentrate.

The compounds of the formula I or the herbicidal compositions can beapplied pre- or post-emergence. If the active ingredients are less welltolerated by certain crop plants, application techniques may be used inwhich the herbicidal compositions are sprayed, with the aid of thespraying equipment, in such a way that as far as possible they do notcome into contact with the leaves of the sensitive crop plants, whilethe active ingredients reach the leaves of undesirable plants growingunderneath, or the bare soil surface (post-directed, lay-by).

The rates of application of the compound of the formula I are from 0.001to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.),depending on the control target, the season, the target plants and thegrowth stage.

To widen the spectrum of action and to achieve synergistic effects, thebenzoyl-substituted serineamides of the formula I may be mixed with alarge number of representatives of other herbicidal or growth-regulatingactive ingredient groups and then applied concomitantly. Suitablecomponents for mixtures are, for example, 1,2,4-thiadiazoles,1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives,aminotriazoles, anilides, (het)aryloxyalkanoic acids and theirderivatives, benzoic acid and its derivatives, benzothiadiazinones,2-(het)aroyl-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivatives, diazines, dichloropropionic acidand its derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenylpropionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolecarboxamides and uracils.

It may furthermore be beneficial to apply the compounds of the formula Ialone or in combination with other herbicides, or in the form of amixture with other crop protection agents, for example together withagents for controlling pests or phytopathogenic fungi or bacteria. Alsoof interest is the miscibility with mineral salt solutions, which areemployed for treating nutritional and trace element deficiencies.Non-phytotoxic oils and oil concentrates may also be added.

Use Examples

The herbicidal activity of the benzoyl-substituted serineamides of theformula I was demonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants had rooted. This cover causesuniform germination of the test plants, unless this has been impaired bythe active ingredients.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 15 cm, depending on the plant habit, and only thentreated with the active ingredients which had been suspended oremulsified in water. For this purpose, the test plants were either sowndirectly and grown in the same containers, or they were first grownseparately as seedlings and transplanted into the test containers a fewdays prior to treatment. The rate of application for the post-emergencetreatment was 1.0 kg/ha of a.s. (active substance).

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments belonged to the followingspecies:

Scientific name Common Name Amaranthus retroflexus pig weed Chenopodiumalbum lambsquarters Galium aparine cleavers harrif Polygonum convolvulusblack bindweed Setaria viridis green foxtail

At application rates of 1 kg/ha, the compound 3.4 (Table 3) showed verygood post-emergence action against the unwanted plants Amaranthusretroflexus, Chenopodium album, Galium aparine and Polygonumconvolvulus.

Furthermore, compound 3.11 (Table 3), applied by the post-emergencemethod, effected, at application rates of 1 kg/ha, very good control ofthe harmful plants Amaranthus retroflexus, Chenopodium album, Galiumaparine and Polygonum convolvulus.

The activity of compound 3.14 (Table 3), applied by the post-emergencemethod, at application rates of 1 kg/ha, against the unwanted plantsAmaranthus retroflexus, Chenopodium album, Galium aparine and Polygonumconvolvulus was very good.

At application rates of 1 kg/ha, the compound 3.18 (Table 3) showed verygood post-emergence action against the unwanted plants Amaranthusretroflexus, Chenopodium album, Galium aparine and Setaria viridis.

Furthermore, compound 3.56 (Table 3), applied by the post-emergencemethod, effected, at application rates of 1 kg/ha, very good control ofthe harmful plants Amaranthus retroflexus, Chenopodium album, Galiumaparine and Setaria viridis.

1-12. (canceled)
 13. A benzoyl-substituted serineamide of the formula I

wherein R¹ is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl orC₁-C₆-haloalkoxy; R², R³, R⁴, R⁵ are hydrogen, halogen, cyano,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R⁶, R⁷are hydrogen, hydroxyl or C₁-C₆-alkoxy; R⁸ is C₁-C₆-alkyl,C₁-C₄-cyanoalkyl or C₁-C₆-haloalkyl; R⁹ is hydrogen, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-haloalkenyl,C₃-C₆-haloalkynyl, formyl, C₁-C₆-alkylcarbonyl,C₃-C₆-cycloalkylcarbonyl, C₂-C₆-alkenylcarbonyl, C₂-C₆-alkynylcarbonyl,C₁-C₆-alkoxycarbonyl, C₃-C₆-alkenyloxycarbonyl,C₃-C₆-alkynyloxycarbonyl, C₁-C₆-alkylaminocarbonyl,C₃-C₆-alkenylaminocarbonyl, C₃-C₆-alkynylaminocarbonyl,C₁-C₆-alkylsulfonylaminocarbonyl, di(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkyl)aminocarbonyl,N—(C₁-C₆-alkoxy)-N—(C₁-C₆-alkyl)aminocarbonyl,N—(C₃-C₆-alkenyl)-N—(C₁-C₆-alkoxy)aminocarbonyl,N—(C₃-C₆-alkynyl)-N—(C₁-C₆-alkoxy)aminocarbonyl,di(C₁-C₆-alkyl)aminothiocarbonyl, (C₁-C₆-alkyl)cyanoimino,(amino)cyanoimino, [(C₁-C₆-alkyl)amino]cyanoimino,[di(C₁-C₆-alkyl)amino]cyanoimino, C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl,C₁-C₆-alkoxyimino-C₁-C₆-alkyl, N—(C₁-C₆-alkylamino)imino-C₁-C₆-alkyl,N-(di-C₁-C₆-alkylamino)imino-C₁-C₆-alkyl or tri-C₁-C₄-alkylsilyl, wherethe alkyl, cycloalkyl and alkoxy radicals mentioned may be partially orfully halogenated and/or may carry one to three of the following groups:cyano, hydroxyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,di(C₁-C₄-alkyl)amino, C₁-C₄-alkyl-C₁-C₆-alkoxycarbonylamino,C₁-C₄-alkylcarbonyl, hydroxycarbonyl, C₁-C₄-alkoxycarbonyl,aminocarbonyl, C₁-C₄-alkylaminocarbonyl, di(C₁-C₄-alkyl)aminocarbonyl orC₁-C₄-alkylcarbonyloxy; phenyl, phenyl-C₁-C₆-alkyl, phenylcarbonyl,phenylcarbonyl-C₁-C₆-alkyl, phenoxycarbonyl, phenylaminocarbonyl,phenylsulfonylaminocarbonyl, N—(C₁-C₆-alkyl)-N-(phenyl)aminocarbonyl,phenyl-C₁-C₆-alkylcarbonyl, where the phenyl radical may be partially orfully halogenated and/or may carry one to three of the following groups:nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy; or SO₂R¹²; R¹⁰ is hydrogen or C₁-C₆-alkyl; R¹¹ isC₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-cyanoalkyl,C₂-C₆-cyanoalkenyl, C₂-C₆-cyanoalkynyl, C₁-C₆-hydroxyalkyl,C₂-C₆-hydroxyalkenyl, C₂-C₆-hydroxyalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkenyl, 3- to 6-membered heterocyclyl, 3- to 6-memberedheterocyclyl-C₁-C₄-alkyl, wherein the cycloalkyl, cycloalkenyl or 3- to6-membered heterocyclyl radicals mentioned above may be partially orfully halogenated and/or may carry one to three radicals from the groupconsisting of oxo, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, hydroxycarbonyl, C₁-C₆-alkoxycarbonyl,hydroxycarbonyl-C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl-C₁-C₆-alkoxy, amino,C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylsulfonylamino,C₁-C₆-haloalkylsulfonylamino, aminocarbonylamino,(C₁-C₆-alkylamino)carbonylamino, di(C₁-C₆-alkyl)-aminocarbonylamino,aryl and aryl(C₁-C₆-alkyl); C₁-C₆-alkoxy-C₁-C₄-alkyl,C₂-C₆-alkenyloxy-C₁-C₄-alkyl, C₂-C₆-alkynyloxy-C₁-C₄-alkyl,C₁-C₆-haloalkoxy-C₁-C₄-alkyl, C₂-C₆-haloalkenyloxy-C₁-C₄-alkyl,C₂-C₆-haloalkynyloxy-C₁-C₄-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₆-alkylthio-C₁-C₄-alkyl, C₂-C₆-alkenylthio-C₁-C₄-alkyl,C₂-C₆-alkynylthio-C₁-C₄-alkyl, C₁-C₆-haloalkyl-C₁-C₄-thioalkyl,C₂-C₆-haloalkenyl-C₁-C₄-thioalkyl, C₂-C₆-haloalkynyl-C₁-C₄-thioalkyl,C₁-C₆-alkylsulfinyl-C₁-C₄-alkyl, C₁-C₆-haloalkylsulfinyl-C₁-C₄-alkyl,C₁-C₆-alkylsulfonyl-C₁-C₄-alkyl, C₁-C₆-haloalkylsulfonyl-C₁-C₄-alkyl,amino-C₁-C₄-alkyl, C₁-C₆-alkylamino-C₁-C₄-alkyl,di(C₁-C₆-alkyl)amino-C₁-C₄-alkyl, C₁-C₆-alkylsulfonylamino-C₁-C₄-alkyl,C₁-C₆-alkylsulfonyl-(C₁-C₆-alkylamino)-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl,hydroxycarbonyl, C₁-C₆-alkoxycarbonyl, aminocarbonyl,C₁-C₆-alkylaminocarbonyl, di(C₁-C₆-alkyl)aminocarbonyl,C₁-C₆-alkylcarbonyl-C₁-C₆-alkyl, hydroxycarbonyl-C₁-C₄-alkyl,C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₆-haloalkoxycarbonyl-C₁-C₄-alkyl,C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl, aminocarbonyl-C₁-C₄-alkyl,C₁-C₆-alkylaminocarbonyl-C₁-C₄-alkyl,di(C₁-C₆-alkyl)aminocarbonyl-C₁-C₄-alkyl, formylamino-C₁-C₄-alkyl,C₁-C₆-alkoxycarbonylamino-C₁-C₄-alkyl,C₁-C₆-alkylcarbonylamino-C₁-C₄-alkyl,C₁-C₆-alkylcarbonyl-(C₁-C₆-alkylamino)-C₁-C₄-alkyl,[(C₁-C₆-alkyl)aminocarbonyloxy]-C₁-C₄-alkyl,[di(C₁-C₆-alkyl)aminocarbonyloxy]C₁-C₄-alkyl,{di[di(C₁-C₆-alkyl)amino]carbonyloxy}C₁-C₄-alkyl,[(C₁-C₆-alkylamino)carbonylamino]-C₁-C₄-alkyl,[di(C₁-C₆-alkyl)aminocarbonylamino]C₁-C₄-alkyl; phenyl-C₁-C₄-alkyl,phenyl-C₂-C₄-alkenyl, phenyl-C₂-C₄-alkynyl, phenyl-C₁-C₄-haloalkyl,phenyl-C₂-C₄-haloalkenyl, phenyl-C₂-C₄-haloalkynyl,phenyl-C₁-C₄-hydroxyalkyl, phenyl-C₂-C₄-hydroxyalkenyl,phenyl-C₂-C₄-hydroxyalkynyl, phenylcarbonyl-C₁-C₄-alkyl,phenylcarbonylamino-C₁-C₄-alkyl, phenylcarbonyloxy-C₁-C₄-alkyl,phenyloxycarbonyl-C₁-C₄-alkyl, phenyloxy-C₁-C₄-alkyl,phenylthio-C₁-C₄-alkyl, phenylsulfinyl-C₁-C₄-alkyl,phenylsulfonyl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-alkyl,heteroaryl-C₂-C₄-alkenyl, heteroaryl-C₂-C₄-alkynyl,heteroaryl-C₁-C₄-haloalkyl, heteroaryl-C₂-C₄-haloalkenyl,heteroaryl-C₂-C₄-haloalkynyl, heteroaryl-C₁-C₄-hydroxyalkyl,heteroaryl-C₂-C₄-hydroxyalkenyl, heteroaryl-C₂-C₄-hydroxyalkynyl,heteroarylcarbonyl-C₁-C₄-alkyl, heteroarylcarbonyloxy-C₁-C₄-alkyl,heteroaryloxycarbonyl-C₁-C₄-alkyl, heteroaryloxy-C₁-C₄-alkyl,heteroarylthio-C₁-C₄-alkyl, heteroarylsulfinyl-C₁-C₄-alkyl,heteroarylsulfonyl-C₁-C₄-alkyl, where the phenyl and heteroaryl radicalsmentioned above may be partially or fully halogenated and/or may carryone to three radicals from the group consisting of cyano, nitro,C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxy, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,hydroxycarbonyl, C₁-C₆-alkoxycarbonyl, hydroxycarbonyl-C₁-C₆-alkoxy,C₁-C₆-alkoxycarbonyl-C₁-C₆-alkoxy, amino, C₁-C₆-alkylamino,di(C₁-C₆-alkyl)amino, C₁-C₆-alkylsulfonylamino,C₁-C₆-haloalkylsulfonylamino, (C₁-C₆-alkylamino)carbonylamino,di(C₁-C₆-alkyl)aminocarbonylamino, aryl and aryl(C₁-C₆-alkyl); R¹² isC₁-C₆-alkyl, C₁-C₆-haloalkyl or phenyl, where the phenyl radical may bepartially or fully halogenated and/or may carry one to three of thefollowing groups: C₁-C₆-alkyl, C₁-C₆-haloalkyl or C₁-C₆-alkoxy; or anagriculturally useful salt thereof.
 14. The benzoyl-substitutedserineamide of the formula I according to claim 13 where R¹ is halogenor C₁-C₆-haloalkyl.
 15. The benzoyl-substituted serineamide of theformula I according to claim 13 where R² and R³ independently of oneanother are hydrogen, halogen or C₁-C₆-haloalkyl.
 16. Thebenzoyl-substituted serineamide of the formula I according to claim 13where R⁴, R⁵, R⁶, R⁷ and R¹⁰ are hydrogen.
 17. The benzoyl-substitutedserineamide of the formula I according to claim 13 where R¹¹ isC₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₆-cyanoalkyl,C₁-C₆-hydroxyalkyl, C₂-C₆-hydroxyalkenyl, C₂-C₆-hydroxyalkynyl,C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, 3- to 6-membered heterocyclyl,wherein the cycloalkyl, cycloalkenyl or 3- to 6-membered heterocyclylradicals mentioned above may be partially or fully halogenated and/ormay carry one to three radicals from the group consisting of oxo,C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxycarbonyl and C₁-C₆-alkoxycarbonyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-haloalkoxy-C₁-C₄-alkyl,C₁-C₆-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl,C₁-C₆-alkylsulfonylamino-C₁-C₄-alkyl, hydroxycarbonyl,C₁-C₆-alkoxycarbonyl, hydroxycarbonyl-C₁-C₄-alkyl,C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₆-haloalkoxycarbonyl-C₁-C₄-alkyl,C₁-C₆-alkylcarbonyloxy-C₁-C₄-alkyl,C₁-C₆-alkylcarbonylamino-C₁-C₄-alkyl,di(C₁-C₆-alkyl)carbonylamino-C₁-C₄-alkyl,[di(C₁-C₆-alkyl)aminocarbonylamino]-C₁-C₄-alkyl,[(C₁-C₆-alkyl)aminocarbonyl]amino-C₁-C₄-alkyl,[di(C₁-C₆-alkyl)aminocarbonyloxy]-C₁-C₄-alkyl, formylamino-C₁-C₄-alkyl,phenyl-C₁-C₄-alkyl, phenyl-C₂-C₄-alkenyl, phenyl-C₂-C₄-alkynyl,phenyl-C₁-C₄-haloalkyl, phenyl-C₂-C₄-haloalkenyl,phenyl-C₁-C₄-hydroxyalkyl, phenyloxy-C₁-C₄-alkyl,phenylthio-C₁-C₄-alkyl, phenylsulfinyl-C₁-C₄-alkyl,phenylsulfonyl-C₁-C₄-alkyl, heteroaryl-C₁-C₄-alkyl,heteroaryl-C₁-C₄-hydroxyalkyl, heteroaryloxy-C₁-C₄-alkyl,heteroarylthio-C₁-C₄-alkyl, heteroarylsulfinyl-C₁-C₄-alkyl,heteroarylsulfonyl-C₁-C₄-alkyl, where the phenyl and heteroaryl radicalsmentioned above may be partially or fully halogenated and/or may carryone to three radicals from the group consisting of cyano, nitro,C₁-C₆-alkyl, C₁-C₆-haloalkyl, hydroxy, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,hydroxycarbonyl, C₁-C₆-alkoxycarbonyl, hydroxycarbonyl-C₁-C₆-alkoxy,C₁-C₆-alkylsulfonylamino and C₁-C₆-haloalkylsulfonylamino.
 18. A processfor preparing benzoyl-substituted serineamides of the formula Iaccording to claim 13, wherein serine derivatives of the formula V

where R⁶, R⁹, R¹⁰ and R¹¹ are as defined in claim 13 and L¹ is hydroxylor C₁-C₆-alkoxy are reacted with benzoic acids/benzoic acid derivativesof the formula IV

where R¹ to R⁵ are as defined in claim 13 and L² is hydroxyl, halogen,C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₄-alkylsulfonyl,phosphoryl or isoureyl to give the corresponding benzoyl derivatives ofthe formula III

where R¹ to R⁶ and R⁹ to R¹¹ are as defined in claim 1 and L¹ ishydroxyl or C₁-C₆-alkoxy and the resulting benzoyl derivatives of theformula III are then reacted with an amine of the formula IIHNR⁷R⁸  II, where R⁷ and R⁸ are as defined in claim
 13. 19. A processfor preparing benzoyl-substituted serineamides of the formula Iaccording to claim 18 where R⁹ and R¹⁰ are hydrogen, wherein benzoylderivatives of the formula III where R⁹ and R¹⁰ are hydrogen areprepared by acylation of keto compounds of the formula XIII

where R⁶ and R¹¹ are as defined in claim 13 and L¹ is hydroxyl orC₁-C₆-alkoxy with benzoic acids/benzoic acid derivatives of the formulaIV to give N-acyl keto compounds of the formula XII

where R¹ to R⁶ and R¹¹ are as defined in claim 13 and L¹ is hydroxyl orC₁-C₆-alkoxy and subsequent reduction of the keto group.
 20. A benzoylderivative of the formula III

where R¹ is fluorine, chlorine or CF₃; R² to R⁶ and R⁹ to R¹¹ are asdefined in claim 13 and L¹ is hydroxyl or C₁-C₆-alkoxy
 21. Acomposition, comprising a herbicidally effective amount of at least onebenzoyl-substituted serineamide of the formula I or an agriculturallyuseful salt of formula I according to claim 13 and auxiliaries customaryfor formulating crop protection agents.
 22. A process for preparingcompositions according to claim 21, wherein a herbicidally effectiveamount of at least one benzoyl-substituted serineamide of the formula Ior an agriculturally useful salt of formula I according to claim 13 andauxiliaries customary for formulating crop protection agents are mixed.23. A method for controlling unwanted vegetation, wherein a herbicidallyeffective amount of at least one benzoyl-substituted serineamide of theformula I or an agriculturally useful salt of formula I according toclaim 13 is allowed to act on plants, their habitat and/or on seed.